@librechat/agents 2.3.0 → 2.3.1

package/dist/cjs/messages/prune.cjs

@@ -204,24 +204,48 @@ function getMessagesWithinTokenLimit({ messages: _messages, maxContextTokens, in
                     }
                 }
             }
-            // If the latest message is an assistant message, ensure an assistant message appears early in the context
-            // but maintain system message precedence
+            // If the latest message is an assistant message, ensure an assistant message with thinking appears at the end
+            // of the context (which will become the beginning after reversal)
+            // but maintain system message precedence after reversal
             if (latestMessageIsAssistant && context.length > 0) {
-                // Find the first assistant message in the context
-                const assistantIndex = context.findIndex(msg => msg.getType() === 'ai');
-                if (assistantIndex > 0) {
-                    // Check if there's a system message at the beginning
-                    const hasSystemFirst = context[0].getType() === 'system';
-                    // Move the assistant message to the appropriate position
-                    const assistantMsg = context[assistantIndex];
-                    context.splice(assistantIndex, 1);
-                    if (hasSystemFirst) {
-                        // Insert after the system message
-                        context.splice(1, 0, assistantMsg);
+                // Find assistant messages with thinking blocks
+                const assistantIndices = [];
+                for (let i = 0; i < context.length; i++) {
+                    const msg = context[i];
+                    if (msg.getType() === 'ai') {
+                        const hasThinking = Array.isArray(msg.content) &&
+                            msg.content.some(item => item && typeof item === 'object' && item.type === 'thinking');
+                        if (hasThinking) {
+                            assistantIndices.push(i);
+                        }
+                    }
+                }
+                // If we found assistant messages with thinking blocks
+                if (assistantIndices.length > 0) {
+                    // Get the first assistant message with thinking
+                    const assistantWithThinkingIndex = assistantIndices[0];
+                    const assistantWithThinking = context[assistantWithThinkingIndex];
+                    // Remove it from its current position
+                    context.splice(assistantWithThinkingIndex, 1);
+                    // Check if there's a system message in the context
+                    const systemIndex = context.findIndex(msg => msg.getType() === 'system');
+                    const hasSystem = systemIndex !== -1;
+                    if (hasSystem) {
+                        // We want the system message to be first after reversal
+                        // This means we need to put it at the end position before reversal
+                        // And the assistant message should be second after reversal
+                        // This means we need to put it at the end - 1 position before reversal
+                        // First, ensure the system message is at the end (will be first after reversal)
+                        const systemMsg = context[systemIndex];
+                        context.splice(systemIndex, 1);
+                        context.push(systemMsg);
+                        // Then, put the assistant message right before the system message (will be second after reversal)
+                        context.splice(context.length - 1, 0, assistantWithThinking);
                     }
                     else {
-                        // Insert at the beginning if no system message
-                        context.unshift(assistantMsg);
+                        // No system message, so we want assistant to be first after reversal
+                        // This means we need to put it at the end position before reversal
+                        context.push(assistantWithThinking);
                     }
                 }
             }

package/dist/cjs/messages/prune.cjs.map

@@ -1 +1 @@
-{"version":3,"file":"prune.cjs","sources":["../../../src/messages/prune.ts"],"sourcesContent":["import { AIMessage } from '@langchain/core/messages';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { TokenCounter } from '@/types/run';\nexport type PruneMessagesFactoryParams = {\n  maxTokens: number;\n  startIndex: number;\n  tokenCounter: TokenCounter;\n  indexTokenCountMap: Record<string, number>;\n  thinkingEnabled?: boolean;\n};\nexport type PruneMessagesParams = {\n  messages: BaseMessage[];\n  usageMetadata?: Partial<UsageMetadata>;\n  startOnMessageType?: ReturnType<BaseMessage['getType']>;\n}\n\n/**\n * Calculates the total tokens from a single usage object\n * \n * @param usage The usage metadata object containing token information\n * @returns An object containing the total input and output tokens\n */\nfunction calculateTotalTokens(usage: Partial<UsageMetadata>): UsageMetadata {\n  const baseInputTokens = Number(usage.input_tokens) || 0;\n  const cacheCreation = Number(usage.input_token_details?.cache_creation) || 0;\n  const cacheRead = Number(usage.input_token_details?.cache_read) || 0;\n  \n  const totalInputTokens = baseInputTokens + cacheCreation + cacheRead;\n  const totalOutputTokens = Number(usage.output_tokens) || 0;\n\n  return {\n    input_tokens: totalInputTokens,\n    output_tokens: totalOutputTokens,\n    total_tokens: totalInputTokens + totalOutputTokens\n  };\n}\n\n/**\n * Processes an array of messages and returns a context of messages that fit within a specified token limit.\n * It iterates over the messages from newest to oldest, adding them to the context until the token limit is reached.\n * \n * @param options Configuration options for processing messages\n * @returns Object containing the message context, remaining tokens, messages not included, and summary index\n */\nfunction getMessagesWithinTokenLimit({\n  messages: _messages,\n  maxContextTokens,\n  indexTokenCountMap,\n  startOnMessageType,\n  thinkingEnabled,\n  tokenCounter,\n}: {\n  messages: BaseMessage[];\n  maxContextTokens: number;\n  indexTokenCountMap: Record<string, number>;\n  startOnMessageType?: string;\n  thinkingEnabled?: boolean;\n  tokenCounter?: TokenCounter;\n}): {\n  context: BaseMessage[];\n  remainingContextTokens: number;\n  messagesToRefine: BaseMessage[];\n  summaryIndex: number;\n} {\n  // Every reply is primed with <|start|>assistant<|message|>, so we\n  // start with 3 tokens for the label after all messages have been counted.\n  let summaryIndex = -1;\n  let currentTokenCount = 3;\n  const instructions = _messages?.[0]?.getType() === 'system' ? _messages[0] : undefined;\n  const instructionsTokenCount = instructions != null ? indexTokenCountMap[0] : 0;\n  let remainingContextTokens = maxContextTokens - instructionsTokenCount;\n  const messages = [..._messages];\n  let context: BaseMessage[] = [];\n\n  if (currentTokenCount < remainingContextTokens) {\n    let currentIndex = messages.length;\n    while (messages.length > 0 && currentTokenCount < remainingContextTokens && currentIndex > 1) {\n      currentIndex--;\n      if (messages.length === 1 && instructions) {\n        break;\n      }\n      const poppedMessage = messages.pop();\n      if (!poppedMessage) continue;\n      \n      const tokenCount = indexTokenCountMap[currentIndex] || 0;\n\n      if ((currentTokenCount + tokenCount) <= remainingContextTokens) {\n        context.push(poppedMessage);\n        currentTokenCount += tokenCount;\n      } else {\n        messages.push(poppedMessage);\n        break;\n      }\n    }\n    \n  // Handle startOnMessageType requirement\n  if (startOnMessageType && context.length > 0) {\n    const requiredTypeIndex = context.findIndex(msg => msg.getType() === startOnMessageType);\n    \n    if (requiredTypeIndex > 0) {\n      context = context.slice(requiredTypeIndex);\n    }\n  }\n  \n  // Add system message if it exists\n  if (instructions && _messages.length > 0) {\n    context.push(_messages[0] as BaseMessage);\n    messages.shift();\n  }\n  \n  // Handle thinking mode requirement for Anthropic\n  if (thinkingEnabled && context.length > 0 && tokenCounter) {\n    // Check if the latest message is an assistant message\n    const latestMessageIsAssistant = _messages.length > 0 && _messages[_messages.length - 1].getType() === 'ai';\n    \n    // Process only if we have an assistant message in the context\n    const firstAssistantIndex = context.findIndex(msg => msg.getType() === 'ai');\n    \n    if (firstAssistantIndex >= 0) {\n      const firstAssistantMsg = context[firstAssistantIndex];\n      \n      // Check if the first assistant message already has a thinking block\n      const hasThinkingBlock = Array.isArray(firstAssistantMsg.content) && \n        firstAssistantMsg.content.some(item => \n          item && typeof item === 'object' && item.type === 'thinking');\n      \n      // Only proceed if we need to add thinking blocks\n      if (!hasThinkingBlock) {\n        // Collect thinking blocks from pruned assistant messages, starting from the most recent\n        const thinkingBlocks: any[] = [];\n        \n        // Look through pruned messages for thinking blocks, starting from the end (most recent)\n        for (let i = messages.length - 1; i >= 0; i--) {\n          const msg = messages[i];\n          if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n            for (const item of msg.content) {\n              if (item && typeof item === 'object' && item.type === 'thinking') {\n                thinkingBlocks.push(item);\n                // We only need one thinking block\n                break;\n              }\n            }\n            if (thinkingBlocks.length > 0) break; // Stop after finding one thinking block\n          }\n        }\n        \n        // If we found thinking blocks, add them to the first assistant message\n        if (thinkingBlocks.length > 0) {\n          // Calculate token count of original message\n          const originalTokenCount = tokenCounter(firstAssistantMsg);\n          \n          // Create a new content array with thinking blocks at the beginning\n          let newContent: any[];\n          \n          if (Array.isArray(firstAssistantMsg.content)) {\n            // Keep the original content (excluding any existing thinking blocks)\n            const originalContent = firstAssistantMsg.content.filter(item => \n              !(item && typeof item === 'object' && item.type === 'thinking'));\n            \n            newContent = [...thinkingBlocks, ...originalContent];\n          } else if (typeof firstAssistantMsg.content === 'string') {\n            newContent = [\n              ...thinkingBlocks,\n              { type: 'text', text: firstAssistantMsg.content }\n            ];\n          } else {\n            newContent = thinkingBlocks;\n          }\n          \n          // Create a new message with the updated content\n          const newMessage = new AIMessage({\n            content: newContent,\n            additional_kwargs: firstAssistantMsg.additional_kwargs,\n            response_metadata: firstAssistantMsg.response_metadata,\n          });\n          \n          // Calculate token count of new message\n          const newTokenCount = tokenCounter(newMessage);\n          \n          // Adjust current token count\n          currentTokenCount += (newTokenCount - originalTokenCount);\n          \n          // Replace the first assistant message\n          context[firstAssistantIndex] = newMessage;\n          \n          // If we've exceeded the token limit, we need to prune more messages\n          if (currentTokenCount > remainingContextTokens) {\n            // Build a map of tool call IDs to track AI <--> tool message correspondences\n            const toolCallIdMap = new Map<string, number>();\n            \n            // Identify tool call IDs in the context\n            for (let i = 0; i < context.length; i++) {\n              const msg = context[i];\n              \n              // Check for tool calls in AI messages\n              if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n                for (const item of msg.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    toolCallIdMap.set(item.id, i);\n                  }\n                }\n              }\n              \n              // Check for tool messages\n              if (msg.getType() === 'tool' && 'tool_call_id' in msg && typeof msg.tool_call_id === 'string') {\n                toolCallIdMap.set(msg.tool_call_id, i);\n              }\n            }\n            \n            // Track which messages to remove\n            const indicesToRemove = new Set<number>();\n            \n            // Start removing messages from the end, but preserve AI <--> tool message correspondences\n            let i = context.length - 1;\n            while (i > firstAssistantIndex && currentTokenCount > remainingContextTokens) {\n              const msgToRemove = context[i];\n              \n              // Check if this is a tool message or has tool calls\n              let canRemove = true;\n              \n              if (msgToRemove.getType() === 'tool' && 'tool_call_id' in msgToRemove && typeof msgToRemove.tool_call_id === 'string') {\n                // If this is a tool message, check if we need to keep its corresponding AI message\n                const aiIndex = toolCallIdMap.get(msgToRemove.tool_call_id);\n                if (aiIndex !== undefined && aiIndex !== i && !indicesToRemove.has(aiIndex)) {\n                  // We need to remove both the tool message and its corresponding AI message\n                  indicesToRemove.add(i);\n                  indicesToRemove.add(aiIndex);\n                  currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[aiIndex]));\n                  canRemove = false;\n                }\n              } else if (msgToRemove.getType() === 'ai' && Array.isArray(msgToRemove.content)) {\n                // If this is an AI message with tool calls, check if we need to keep its corresponding tool messages\n                for (const item of msgToRemove.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    const toolIndex = toolCallIdMap.get(item.id as string);\n                    if (toolIndex !== undefined && toolIndex !== i && !indicesToRemove.has(toolIndex)) {\n                      // We need to remove both the AI message and its corresponding tool message\n                      indicesToRemove.add(i);\n                      indicesToRemove.add(toolIndex);\n                      currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[toolIndex]));\n                      canRemove = false;\n                      break;\n                    }\n                  }\n                }\n              }\n              \n              // If we can remove this message individually\n              if (canRemove && !indicesToRemove.has(i)) {\n                indicesToRemove.add(i);\n                currentTokenCount -= tokenCounter(msgToRemove);\n              }\n              \n              i--;\n            }\n            \n            // Remove messages in reverse order to avoid index shifting\n            const sortedIndices = Array.from(indicesToRemove).sort((a, b) => b - a);\n            for (const index of sortedIndices) {\n              context.splice(index, 1);\n            }\n            \n            // Update remainingContextTokens to reflect the new token count\n            remainingContextTokens = maxContextTokens - currentTokenCount;\n          }\n        }\n      }\n    }\n    \n    // If the latest message is an assistant message, ensure an assistant message appears early in the context\n    // but maintain system message precedence\n    if (latestMessageIsAssistant && context.length > 0) {\n      // Find the first assistant message in the context\n      const assistantIndex = context.findIndex(msg => msg.getType() === 'ai');\n      if (assistantIndex > 0) {\n        // Check if there's a system message at the beginning\n        const hasSystemFirst = context[0].getType() === 'system';\n        \n        // Move the assistant message to the appropriate position\n        const assistantMsg = context[assistantIndex];\n        context.splice(assistantIndex, 1);\n        \n        if (hasSystemFirst) {\n          // Insert after the system message\n          context.splice(1, 0, assistantMsg);\n        } else {\n          // Insert at the beginning if no system message\n          context.unshift(assistantMsg);\n        }\n      }\n    }\n  }\n  }\n\n  const prunedMemory = messages;\n  summaryIndex = prunedMemory.length - 1;\n  remainingContextTokens -= currentTokenCount;\n\n  return {\n    summaryIndex,\n    remainingContextTokens,\n    context: context.reverse(),\n    messagesToRefine: prunedMemory,\n  };\n}\n\nfunction checkValidNumber(value: unknown): value is number {\n  return typeof value === 'number' && !isNaN(value) && value > 0;\n}\n\nexport function createPruneMessages(factoryParams: PruneMessagesFactoryParams) {\n  const indexTokenCountMap = { ...factoryParams.indexTokenCountMap };\n  let lastTurnStartIndex = factoryParams.startIndex;\n  let totalTokens = (Object.values(indexTokenCountMap)).reduce((a, b) => a + b, 0);\n  \n  return function pruneMessages(params: PruneMessagesParams): {\n    context: BaseMessage[];\n    indexTokenCountMap: Record<string, number>;\n  } {\n    let currentUsage: UsageMetadata | undefined;\n    if (params.usageMetadata && (\n      checkValidNumber(params.usageMetadata.input_tokens)\n      || (\n        checkValidNumber(params.usageMetadata.input_token_details)\n        && (\n          checkValidNumber(params.usageMetadata.input_token_details.cache_creation)\n          || checkValidNumber(params.usageMetadata.input_token_details.cache_read)\n        )\n      )\n    ) && checkValidNumber(params.usageMetadata.output_tokens)) {\n      currentUsage = calculateTotalTokens(params.usageMetadata);\n      totalTokens = currentUsage.total_tokens;\n    }\n\n    for (let i = lastTurnStartIndex; i < params.messages.length; i++) {\n      const message = params.messages[i];\n      if (i === lastTurnStartIndex && indexTokenCountMap[i] === undefined && currentUsage) {\n        indexTokenCountMap[i] = currentUsage.output_tokens;\n      } else if (indexTokenCountMap[i] === undefined) {\n        indexTokenCountMap[i] = factoryParams.tokenCounter(message);\n        totalTokens += indexTokenCountMap[i];\n      }\n    }\n\n    // If `currentUsage` is defined, we need to distribute the current total tokensto our `indexTokenCountMap`,\n    // for all message index keys before `lastTurnStartIndex`, as it has the most accurate count for those messages.\n    // We must distribute it in a weighted manner, so that the total token count is equal to `currentUsage.total_tokens`,\n    // relative the manually counted tokens in `indexTokenCountMap`.\n    if (currentUsage) {\n      const totalIndexTokens = Object.values(indexTokenCountMap).reduce((a, b) => a + b, 0);\n      const ratio = currentUsage.total_tokens / totalIndexTokens;\n      for (const key in indexTokenCountMap) {\n        indexTokenCountMap[key] = Math.round(indexTokenCountMap[key] * ratio);\n      }\n    }\n\n    lastTurnStartIndex = params.messages.length;\n    if (totalTokens <= factoryParams.maxTokens) {\n      return { context: params.messages, indexTokenCountMap };\n    }\n\n    // Pass the tokenCounter to getMessagesWithinTokenLimit for token recalculation\n    const { context } = getMessagesWithinTokenLimit({\n      maxContextTokens: factoryParams.maxTokens,\n      messages: params.messages,\n      indexTokenCountMap,\n      startOnMessageType: params.startOnMessageType,\n      thinkingEnabled: factoryParams.thinkingEnabled,\n      tokenCounter: factoryParams.tokenCounter,\n    });\n\n    return { context, indexTokenCountMap };\n  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+{"version":3,"file":"prune.cjs","sources":["../../../src/messages/prune.ts"],"sourcesContent":["import { AIMessage } from '@langchain/core/messages';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { TokenCounter } from '@/types/run';\nexport type PruneMessagesFactoryParams = {\n  maxTokens: number;\n  startIndex: number;\n  tokenCounter: TokenCounter;\n  indexTokenCountMap: Record<string, number>;\n  thinkingEnabled?: boolean;\n};\nexport type PruneMessagesParams = {\n  messages: BaseMessage[];\n  usageMetadata?: Partial<UsageMetadata>;\n  startOnMessageType?: ReturnType<BaseMessage['getType']>;\n}\n\n/**\n * Calculates the total tokens from a single usage object\n * \n * @param usage The usage metadata object containing token information\n * @returns An object containing the total input and output tokens\n */\nfunction calculateTotalTokens(usage: Partial<UsageMetadata>): UsageMetadata {\n  const baseInputTokens = Number(usage.input_tokens) || 0;\n  const cacheCreation = Number(usage.input_token_details?.cache_creation) || 0;\n  const cacheRead = Number(usage.input_token_details?.cache_read) || 0;\n  \n  const totalInputTokens = baseInputTokens + cacheCreation + cacheRead;\n  const totalOutputTokens = Number(usage.output_tokens) || 0;\n\n  return {\n    input_tokens: totalInputTokens,\n    output_tokens: totalOutputTokens,\n    total_tokens: totalInputTokens + totalOutputTokens\n  };\n}\n\n/**\n * Processes an array of messages and returns a context of messages that fit within a specified token limit.\n * It iterates over the messages from newest to oldest, adding them to the context until the token limit is reached.\n * \n * @param options Configuration options for processing messages\n * @returns Object containing the message context, remaining tokens, messages not included, and summary index\n */\nfunction getMessagesWithinTokenLimit({\n  messages: _messages,\n  maxContextTokens,\n  indexTokenCountMap,\n  startOnMessageType,\n  thinkingEnabled,\n  tokenCounter,\n}: {\n  messages: BaseMessage[];\n  maxContextTokens: number;\n  indexTokenCountMap: Record<string, number>;\n  startOnMessageType?: string;\n  thinkingEnabled?: boolean;\n  tokenCounter?: TokenCounter;\n}): {\n  context: BaseMessage[];\n  remainingContextTokens: number;\n  messagesToRefine: BaseMessage[];\n  summaryIndex: number;\n} {\n  // Every reply is primed with <|start|>assistant<|message|>, so we\n  // start with 3 tokens for the label after all messages have been counted.\n  let summaryIndex = -1;\n  let currentTokenCount = 3;\n  const instructions = _messages?.[0]?.getType() === 'system' ? _messages[0] : undefined;\n  const instructionsTokenCount = instructions != null ? indexTokenCountMap[0] : 0;\n  let remainingContextTokens = maxContextTokens - instructionsTokenCount;\n  const messages = [..._messages];\n  let context: BaseMessage[] = [];\n\n  if (currentTokenCount < remainingContextTokens) {\n    let currentIndex = messages.length;\n    while (messages.length > 0 && currentTokenCount < remainingContextTokens && currentIndex > 1) {\n      currentIndex--;\n      if (messages.length === 1 && instructions) {\n        break;\n      }\n      const poppedMessage = messages.pop();\n      if (!poppedMessage) continue;\n      \n      const tokenCount = indexTokenCountMap[currentIndex] || 0;\n\n      if ((currentTokenCount + tokenCount) <= remainingContextTokens) {\n        context.push(poppedMessage);\n        currentTokenCount += tokenCount;\n      } else {\n        messages.push(poppedMessage);\n        break;\n      }\n    }\n    \n  // Handle startOnMessageType requirement\n  if (startOnMessageType && context.length > 0) {\n    const requiredTypeIndex = context.findIndex(msg => msg.getType() === startOnMessageType);\n    \n    if (requiredTypeIndex > 0) {\n      context = context.slice(requiredTypeIndex);\n    }\n  }\n  \n  // Add system message if it exists\n  if (instructions && _messages.length > 0) {\n    context.push(_messages[0] as BaseMessage);\n    messages.shift();\n  }\n  \n  // Handle thinking mode requirement for Anthropic\n  if (thinkingEnabled && context.length > 0 && tokenCounter) {\n    // Check if the latest message is an assistant message\n    const latestMessageIsAssistant = _messages.length > 0 && _messages[_messages.length - 1].getType() === 'ai';\n    \n    // Process only if we have an assistant message in the context\n    const firstAssistantIndex = context.findIndex(msg => msg.getType() === 'ai');\n    \n    if (firstAssistantIndex >= 0) {\n      const firstAssistantMsg = context[firstAssistantIndex];\n      \n      // Check if the first assistant message already has a thinking block\n      const hasThinkingBlock = Array.isArray(firstAssistantMsg.content) && \n        firstAssistantMsg.content.some(item => \n          item && typeof item === 'object' && item.type === 'thinking');\n      \n      // Only proceed if we need to add thinking blocks\n      if (!hasThinkingBlock) {\n        // Collect thinking blocks from pruned assistant messages, starting from the most recent\n        const thinkingBlocks: any[] = [];\n        \n        // Look through pruned messages for thinking blocks, starting from the end (most recent)\n        for (let i = messages.length - 1; i >= 0; i--) {\n          const msg = messages[i];\n          if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n            for (const item of msg.content) {\n              if (item && typeof item === 'object' && item.type === 'thinking') {\n                thinkingBlocks.push(item);\n                // We only need one thinking block\n                break;\n              }\n            }\n            if (thinkingBlocks.length > 0) break; // Stop after finding one thinking block\n          }\n        }\n        \n        // If we found thinking blocks, add them to the first assistant message\n        if (thinkingBlocks.length > 0) {\n          // Calculate token count of original message\n          const originalTokenCount = tokenCounter(firstAssistantMsg);\n          \n          // Create a new content array with thinking blocks at the beginning\n          let newContent: any[];\n          \n          if (Array.isArray(firstAssistantMsg.content)) {\n            // Keep the original content (excluding any existing thinking blocks)\n            const originalContent = firstAssistantMsg.content.filter(item => \n              !(item && typeof item === 'object' && item.type === 'thinking'));\n            \n            newContent = [...thinkingBlocks, ...originalContent];\n          } else if (typeof firstAssistantMsg.content === 'string') {\n            newContent = [\n              ...thinkingBlocks,\n              { type: 'text', text: firstAssistantMsg.content }\n            ];\n          } else {\n            newContent = thinkingBlocks;\n          }\n          \n          // Create a new message with the updated content\n          const newMessage = new AIMessage({\n            content: newContent,\n            additional_kwargs: firstAssistantMsg.additional_kwargs,\n            response_metadata: firstAssistantMsg.response_metadata,\n          });\n          \n          // Calculate token count of new message\n          const newTokenCount = tokenCounter(newMessage);\n          \n          // Adjust current token count\n          currentTokenCount += (newTokenCount - originalTokenCount);\n          \n          // Replace the first assistant message\n          context[firstAssistantIndex] = newMessage;\n          \n          // If we've exceeded the token limit, we need to prune more messages\n          if (currentTokenCount > remainingContextTokens) {\n            // Build a map of tool call IDs to track AI <--> tool message correspondences\n            const toolCallIdMap = new Map<string, number>();\n            \n            // Identify tool call IDs in the context\n            for (let i = 0; i < context.length; i++) {\n              const msg = context[i];\n              \n              // Check for tool calls in AI messages\n              if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n                for (const item of msg.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    toolCallIdMap.set(item.id, i);\n                  }\n                }\n              }\n              \n              // Check for tool messages\n              if (msg.getType() === 'tool' && 'tool_call_id' in msg && typeof msg.tool_call_id === 'string') {\n                toolCallIdMap.set(msg.tool_call_id, i);\n              }\n            }\n            \n            // Track which messages to remove\n            const indicesToRemove = new Set<number>();\n            \n            // Start removing messages from the end, but preserve AI <--> tool message correspondences\n            let i = context.length - 1;\n            while (i > firstAssistantIndex && currentTokenCount > remainingContextTokens) {\n              const msgToRemove = context[i];\n              \n              // Check if this is a tool message or has tool calls\n              let canRemove = true;\n              \n              if (msgToRemove.getType() === 'tool' && 'tool_call_id' in msgToRemove && typeof msgToRemove.tool_call_id === 'string') {\n                // If this is a tool message, check if we need to keep its corresponding AI message\n                const aiIndex = toolCallIdMap.get(msgToRemove.tool_call_id);\n                if (aiIndex !== undefined && aiIndex !== i && !indicesToRemove.has(aiIndex)) {\n                  // We need to remove both the tool message and its corresponding AI message\n                  indicesToRemove.add(i);\n                  indicesToRemove.add(aiIndex);\n                  currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[aiIndex]));\n                  canRemove = false;\n                }\n              } else if (msgToRemove.getType() === 'ai' && Array.isArray(msgToRemove.content)) {\n                // If this is an AI message with tool calls, check if we need to keep its corresponding tool messages\n                for (const item of msgToRemove.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    const toolIndex = toolCallIdMap.get(item.id as string);\n                    if (toolIndex !== undefined && toolIndex !== i && !indicesToRemove.has(toolIndex)) {\n                      // We need to remove both the AI message and its corresponding tool message\n                      indicesToRemove.add(i);\n                      indicesToRemove.add(toolIndex);\n                      currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[toolIndex]));\n                      canRemove = false;\n                      break;\n                    }\n                  }\n                }\n              }\n              \n              // If we can remove this message individually\n              if (canRemove && !indicesToRemove.has(i)) {\n                indicesToRemove.add(i);\n                currentTokenCount -= tokenCounter(msgToRemove);\n              }\n              \n              i--;\n            }\n            \n            // Remove messages in reverse order to avoid index shifting\n            const sortedIndices = Array.from(indicesToRemove).sort((a, b) => b - a);\n            for (const index of sortedIndices) {\n              context.splice(index, 1);\n            }\n            \n            // Update remainingContextTokens to reflect the new token count\n            remainingContextTokens = maxContextTokens - currentTokenCount;\n          }\n        }\n      }\n    }\n    \n    // If the latest message is an assistant message, ensure an assistant message with thinking appears at the end\n    // of the context (which will become the beginning after reversal)\n    // but maintain system message precedence after reversal\n    if (latestMessageIsAssistant && context.length > 0) {\n      // Find assistant messages with thinking blocks\n      const assistantIndices: number[] = [];\n      for (let i = 0; i < context.length; i++) {\n        const msg = context[i];\n        if (msg.getType() === 'ai') {\n          const hasThinking = Array.isArray(msg.content) && \n            msg.content.some(item => item && typeof item === 'object' && item.type === 'thinking');\n          \n          if (hasThinking) {\n            assistantIndices.push(i);\n          }\n        }\n      }\n      \n      // If we found assistant messages with thinking blocks\n      if (assistantIndices.length > 0) {\n        // Get the first assistant message with thinking\n        const assistantWithThinkingIndex = assistantIndices[0];\n        const assistantWithThinking = context[assistantWithThinkingIndex];\n        \n        // Remove it from its current position\n        context.splice(assistantWithThinkingIndex, 1);\n        \n        // Check if there's a system message in the context\n        const systemIndex = context.findIndex(msg => msg.getType() === 'system');\n        const hasSystem = systemIndex !== -1;\n        \n        if (hasSystem) {\n          // We want the system message to be first after reversal\n          // This means we need to put it at the end position before reversal\n          // And the assistant message should be second after reversal\n          // This means we need to put it at the end - 1 position before reversal\n          \n          // First, ensure the system message is at the end (will be first after reversal)\n          const systemMsg = context[systemIndex];\n          context.splice(systemIndex, 1);\n          context.push(systemMsg);\n          \n          // Then, put the assistant message right before the system message (will be second after reversal)\n          context.splice(context.length - 1, 0, assistantWithThinking);\n        } else {\n          // No system message, so we want assistant to be first after reversal\n          // This means we need to put it at the end position before reversal\n          context.push(assistantWithThinking);\n        }\n      }\n    }\n  }\n  }\n\n  const prunedMemory = messages;\n  summaryIndex = prunedMemory.length - 1;\n  remainingContextTokens -= currentTokenCount;\n\n  return {\n    summaryIndex,\n    remainingContextTokens,\n    context: context.reverse(),\n    messagesToRefine: prunedMemory,\n  };\n}\n\nfunction checkValidNumber(value: unknown): value is number {\n  return typeof value === 'number' && !isNaN(value) && value > 0;\n}\n\nexport function createPruneMessages(factoryParams: PruneMessagesFactoryParams) {\n  const indexTokenCountMap = { ...factoryParams.indexTokenCountMap };\n  let lastTurnStartIndex = factoryParams.startIndex;\n  let totalTokens = (Object.values(indexTokenCountMap)).reduce((a, b) => a + b, 0);\n  \n  return function pruneMessages(params: PruneMessagesParams): {\n    context: BaseMessage[];\n    indexTokenCountMap: Record<string, number>;\n  } {\n    let currentUsage: UsageMetadata | undefined;\n    if (params.usageMetadata && (\n      checkValidNumber(params.usageMetadata.input_tokens)\n      || (\n        checkValidNumber(params.usageMetadata.input_token_details)\n        && (\n          checkValidNumber(params.usageMetadata.input_token_details.cache_creation)\n          || checkValidNumber(params.usageMetadata.input_token_details.cache_read)\n        )\n      )\n    ) && checkValidNumber(params.usageMetadata.output_tokens)) {\n      currentUsage = calculateTotalTokens(params.usageMetadata);\n      totalTokens = currentUsage.total_tokens;\n    }\n\n    for (let i = lastTurnStartIndex; i < params.messages.length; i++) {\n      const message = params.messages[i];\n      if (i === lastTurnStartIndex && indexTokenCountMap[i] === undefined && currentUsage) {\n        indexTokenCountMap[i] = currentUsage.output_tokens;\n      } else if (indexTokenCountMap[i] === undefined) {\n        indexTokenCountMap[i] = factoryParams.tokenCounter(message);\n        totalTokens += indexTokenCountMap[i];\n      }\n    }\n\n    // If `currentUsage` is defined, we need to distribute the current total tokensto our `indexTokenCountMap`,\n    // for all message index keys before `lastTurnStartIndex`, as it has the most accurate count for those messages.\n    // We must distribute it in a weighted manner, so that the total token count is equal to `currentUsage.total_tokens`,\n    // relative the manually counted tokens in `indexTokenCountMap`.\n    if (currentUsage) {\n      const totalIndexTokens = Object.values(indexTokenCountMap).reduce((a, b) => a + b, 0);\n      const ratio = currentUsage.total_tokens / totalIndexTokens;\n      for (const key in indexTokenCountMap) {\n        indexTokenCountMap[key] = Math.round(indexTokenCountMap[key] * ratio);\n      }\n    }\n\n    lastTurnStartIndex = params.messages.length;\n    if (totalTokens <= factoryParams.maxTokens) {\n      return { context: params.messages, indexTokenCountMap };\n    }\n\n    // Pass the tokenCounter to getMessagesWithinTokenLimit for token recalculation\n    const { context } = getMessagesWithinTokenLimit({\n      maxContextTokens: factoryParams.maxTokens,\n      messages: params.messages,\n      indexTokenCountMap,\n      startOnMessageType: params.startOnMessageType,\n      thinkingEnabled: factoryParams.thinkingEnabled,\n      tokenCounter: factoryParams.tokenCounter,\n    });\n\n    return { context, indexTokenCountMap };\n  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package/dist/esm/messages/prune.mjs

@@ -202,24 +202,48 @@ function getMessagesWithinTokenLimit({ messages: _messages, maxContextTokens, in
                     }
                 }
             }
-            // If the latest message is an assistant message, ensure an assistant message appears early in the context
-            // but maintain system message precedence
+            // If the latest message is an assistant message, ensure an assistant message with thinking appears at the end
+            // of the context (which will become the beginning after reversal)
+            // but maintain system message precedence after reversal
             if (latestMessageIsAssistant && context.length > 0) {
-                // Find the first assistant message in the context
-                const assistantIndex = context.findIndex(msg => msg.getType() === 'ai');
-                if (assistantIndex > 0) {
-                    // Check if there's a system message at the beginning
-                    const hasSystemFirst = context[0].getType() === 'system';
-                    // Move the assistant message to the appropriate position
-                    const assistantMsg = context[assistantIndex];
-                    context.splice(assistantIndex, 1);
-                    if (hasSystemFirst) {
-                        // Insert after the system message
-                        context.splice(1, 0, assistantMsg);
+                // Find assistant messages with thinking blocks
+                const assistantIndices = [];
+                for (let i = 0; i < context.length; i++) {
+                    const msg = context[i];
+                    if (msg.getType() === 'ai') {
+                        const hasThinking = Array.isArray(msg.content) &&
+                            msg.content.some(item => item && typeof item === 'object' && item.type === 'thinking');
+                        if (hasThinking) {
+                            assistantIndices.push(i);
+                        }
+                    }
+                }
+                // If we found assistant messages with thinking blocks
+                if (assistantIndices.length > 0) {
+                    // Get the first assistant message with thinking
+                    const assistantWithThinkingIndex = assistantIndices[0];
+                    const assistantWithThinking = context[assistantWithThinkingIndex];
+                    // Remove it from its current position
+                    context.splice(assistantWithThinkingIndex, 1);
+                    // Check if there's a system message in the context
+                    const systemIndex = context.findIndex(msg => msg.getType() === 'system');
+                    const hasSystem = systemIndex !== -1;
+                    if (hasSystem) {
+                        // We want the system message to be first after reversal
+                        // This means we need to put it at the end position before reversal
+                        // And the assistant message should be second after reversal
+                        // This means we need to put it at the end - 1 position before reversal
+                        // First, ensure the system message is at the end (will be first after reversal)
+                        const systemMsg = context[systemIndex];
+                        context.splice(systemIndex, 1);
+                        context.push(systemMsg);
+                        // Then, put the assistant message right before the system message (will be second after reversal)
+                        context.splice(context.length - 1, 0, assistantWithThinking);
                     }
                     else {
-                        // Insert at the beginning if no system message
-                        context.unshift(assistantMsg);
+                        // No system message, so we want assistant to be first after reversal
+                        // This means we need to put it at the end position before reversal
+                        context.push(assistantWithThinking);
                     }
                 }
             }

package/dist/esm/messages/prune.mjs.map

@@ -1 +1 @@
-{"version":3,"file":"prune.mjs","sources":["../../../src/messages/prune.ts"],"sourcesContent":["import { AIMessage } from '@langchain/core/messages';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { TokenCounter } from '@/types/run';\nexport type PruneMessagesFactoryParams = {\n  maxTokens: number;\n  startIndex: number;\n  tokenCounter: TokenCounter;\n  indexTokenCountMap: Record<string, number>;\n  thinkingEnabled?: boolean;\n};\nexport type PruneMessagesParams = {\n  messages: BaseMessage[];\n  usageMetadata?: Partial<UsageMetadata>;\n  startOnMessageType?: ReturnType<BaseMessage['getType']>;\n}\n\n/**\n * Calculates the total tokens from a single usage object\n * \n * @param usage The usage metadata object containing token information\n * @returns An object containing the total input and output tokens\n */\nfunction calculateTotalTokens(usage: Partial<UsageMetadata>): UsageMetadata {\n  const baseInputTokens = Number(usage.input_tokens) || 0;\n  const cacheCreation = Number(usage.input_token_details?.cache_creation) || 0;\n  const cacheRead = Number(usage.input_token_details?.cache_read) || 0;\n  \n  const totalInputTokens = baseInputTokens + cacheCreation + cacheRead;\n  const totalOutputTokens = Number(usage.output_tokens) || 0;\n\n  return {\n    input_tokens: totalInputTokens,\n    output_tokens: totalOutputTokens,\n    total_tokens: totalInputTokens + totalOutputTokens\n  };\n}\n\n/**\n * Processes an array of messages and returns a context of messages that fit within a specified token limit.\n * It iterates over the messages from newest to oldest, adding them to the context until the token limit is reached.\n * \n * @param options Configuration options for processing messages\n * @returns Object containing the message context, remaining tokens, messages not included, and summary index\n */\nfunction getMessagesWithinTokenLimit({\n  messages: _messages,\n  maxContextTokens,\n  indexTokenCountMap,\n  startOnMessageType,\n  thinkingEnabled,\n  tokenCounter,\n}: {\n  messages: BaseMessage[];\n  maxContextTokens: number;\n  indexTokenCountMap: Record<string, number>;\n  startOnMessageType?: string;\n  thinkingEnabled?: boolean;\n  tokenCounter?: TokenCounter;\n}): {\n  context: BaseMessage[];\n  remainingContextTokens: number;\n  messagesToRefine: BaseMessage[];\n  summaryIndex: number;\n} {\n  // Every reply is primed with <|start|>assistant<|message|>, so we\n  // start with 3 tokens for the label after all messages have been counted.\n  let summaryIndex = -1;\n  let currentTokenCount = 3;\n  const instructions = _messages?.[0]?.getType() === 'system' ? _messages[0] : undefined;\n  const instructionsTokenCount = instructions != null ? indexTokenCountMap[0] : 0;\n  let remainingContextTokens = maxContextTokens - instructionsTokenCount;\n  const messages = [..._messages];\n  let context: BaseMessage[] = [];\n\n  if (currentTokenCount < remainingContextTokens) {\n    let currentIndex = messages.length;\n    while (messages.length > 0 && currentTokenCount < remainingContextTokens && currentIndex > 1) {\n      currentIndex--;\n      if (messages.length === 1 && instructions) {\n        break;\n      }\n      const poppedMessage = messages.pop();\n      if (!poppedMessage) continue;\n      \n      const tokenCount = indexTokenCountMap[currentIndex] || 0;\n\n      if ((currentTokenCount + tokenCount) <= remainingContextTokens) {\n        context.push(poppedMessage);\n        currentTokenCount += tokenCount;\n      } else {\n        messages.push(poppedMessage);\n        break;\n      }\n    }\n    \n  // Handle startOnMessageType requirement\n  if (startOnMessageType && context.length > 0) {\n    const requiredTypeIndex = context.findIndex(msg => msg.getType() === startOnMessageType);\n    \n    if (requiredTypeIndex > 0) {\n      context = context.slice(requiredTypeIndex);\n    }\n  }\n  \n  // Add system message if it exists\n  if (instructions && _messages.length > 0) {\n    context.push(_messages[0] as BaseMessage);\n    messages.shift();\n  }\n  \n  // Handle thinking mode requirement for Anthropic\n  if (thinkingEnabled && context.length > 0 && tokenCounter) {\n    // Check if the latest message is an assistant message\n    const latestMessageIsAssistant = _messages.length > 0 && _messages[_messages.length - 1].getType() === 'ai';\n    \n    // Process only if we have an assistant message in the context\n    const firstAssistantIndex = context.findIndex(msg => msg.getType() === 'ai');\n    \n    if (firstAssistantIndex >= 0) {\n      const firstAssistantMsg = context[firstAssistantIndex];\n      \n      // Check if the first assistant message already has a thinking block\n      const hasThinkingBlock = Array.isArray(firstAssistantMsg.content) && \n        firstAssistantMsg.content.some(item => \n          item && typeof item === 'object' && item.type === 'thinking');\n      \n      // Only proceed if we need to add thinking blocks\n      if (!hasThinkingBlock) {\n        // Collect thinking blocks from pruned assistant messages, starting from the most recent\n        const thinkingBlocks: any[] = [];\n        \n        // Look through pruned messages for thinking blocks, starting from the end (most recent)\n        for (let i = messages.length - 1; i >= 0; i--) {\n          const msg = messages[i];\n          if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n            for (const item of msg.content) {\n              if (item && typeof item === 'object' && item.type === 'thinking') {\n                thinkingBlocks.push(item);\n                // We only need one thinking block\n                break;\n              }\n            }\n            if (thinkingBlocks.length > 0) break; // Stop after finding one thinking block\n          }\n        }\n        \n        // If we found thinking blocks, add them to the first assistant message\n        if (thinkingBlocks.length > 0) {\n          // Calculate token count of original message\n          const originalTokenCount = tokenCounter(firstAssistantMsg);\n          \n          // Create a new content array with thinking blocks at the beginning\n          let newContent: any[];\n          \n          if (Array.isArray(firstAssistantMsg.content)) {\n            // Keep the original content (excluding any existing thinking blocks)\n            const originalContent = firstAssistantMsg.content.filter(item => \n              !(item && typeof item === 'object' && item.type === 'thinking'));\n            \n            newContent = [...thinkingBlocks, ...originalContent];\n          } else if (typeof firstAssistantMsg.content === 'string') {\n            newContent = [\n              ...thinkingBlocks,\n              { type: 'text', text: firstAssistantMsg.content }\n            ];\n          } else {\n            newContent = thinkingBlocks;\n          }\n          \n          // Create a new message with the updated content\n          const newMessage = new AIMessage({\n            content: newContent,\n            additional_kwargs: firstAssistantMsg.additional_kwargs,\n            response_metadata: firstAssistantMsg.response_metadata,\n          });\n          \n          // Calculate token count of new message\n          const newTokenCount = tokenCounter(newMessage);\n          \n          // Adjust current token count\n          currentTokenCount += (newTokenCount - originalTokenCount);\n          \n          // Replace the first assistant message\n          context[firstAssistantIndex] = newMessage;\n          \n          // If we've exceeded the token limit, we need to prune more messages\n          if (currentTokenCount > remainingContextTokens) {\n            // Build a map of tool call IDs to track AI <--> tool message correspondences\n            const toolCallIdMap = new Map<string, number>();\n            \n            // Identify tool call IDs in the context\n            for (let i = 0; i < context.length; i++) {\n              const msg = context[i];\n              \n              // Check for tool calls in AI messages\n              if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n                for (const item of msg.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    toolCallIdMap.set(item.id, i);\n                  }\n                }\n              }\n              \n              // Check for tool messages\n              if (msg.getType() === 'tool' && 'tool_call_id' in msg && typeof msg.tool_call_id === 'string') {\n                toolCallIdMap.set(msg.tool_call_id, i);\n              }\n            }\n            \n            // Track which messages to remove\n            const indicesToRemove = new Set<number>();\n            \n            // Start removing messages from the end, but preserve AI <--> tool message correspondences\n            let i = context.length - 1;\n            while (i > firstAssistantIndex && currentTokenCount > remainingContextTokens) {\n              const msgToRemove = context[i];\n              \n              // Check if this is a tool message or has tool calls\n              let canRemove = true;\n              \n              if (msgToRemove.getType() === 'tool' && 'tool_call_id' in msgToRemove && typeof msgToRemove.tool_call_id === 'string') {\n                // If this is a tool message, check if we need to keep its corresponding AI message\n                const aiIndex = toolCallIdMap.get(msgToRemove.tool_call_id);\n                if (aiIndex !== undefined && aiIndex !== i && !indicesToRemove.has(aiIndex)) {\n                  // We need to remove both the tool message and its corresponding AI message\n                  indicesToRemove.add(i);\n                  indicesToRemove.add(aiIndex);\n                  currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[aiIndex]));\n                  canRemove = false;\n                }\n              } else if (msgToRemove.getType() === 'ai' && Array.isArray(msgToRemove.content)) {\n                // If this is an AI message with tool calls, check if we need to keep its corresponding tool messages\n                for (const item of msgToRemove.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    const toolIndex = toolCallIdMap.get(item.id as string);\n                    if (toolIndex !== undefined && toolIndex !== i && !indicesToRemove.has(toolIndex)) {\n                      // We need to remove both the AI message and its corresponding tool message\n                      indicesToRemove.add(i);\n                      indicesToRemove.add(toolIndex);\n                      currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[toolIndex]));\n                      canRemove = false;\n                      break;\n                    }\n                  }\n                }\n              }\n              \n              // If we can remove this message individually\n              if (canRemove && !indicesToRemove.has(i)) {\n                indicesToRemove.add(i);\n                currentTokenCount -= tokenCounter(msgToRemove);\n              }\n              \n              i--;\n            }\n            \n            // Remove messages in reverse order to avoid index shifting\n            const sortedIndices = Array.from(indicesToRemove).sort((a, b) => b - a);\n            for (const index of sortedIndices) {\n              context.splice(index, 1);\n            }\n            \n            // Update remainingContextTokens to reflect the new token count\n            remainingContextTokens = maxContextTokens - currentTokenCount;\n          }\n        }\n      }\n    }\n    \n    // If the latest message is an assistant message, ensure an assistant message appears early in the context\n    // but maintain system message precedence\n    if (latestMessageIsAssistant && context.length > 0) {\n      // Find the first assistant message in the context\n      const assistantIndex = context.findIndex(msg => msg.getType() === 'ai');\n      if (assistantIndex > 0) {\n        // Check if there's a system message at the beginning\n        const hasSystemFirst = context[0].getType() === 'system';\n        \n        // Move the assistant message to the appropriate position\n        const assistantMsg = context[assistantIndex];\n        context.splice(assistantIndex, 1);\n        \n        if (hasSystemFirst) {\n          // Insert after the system message\n          context.splice(1, 0, assistantMsg);\n        } else {\n          // Insert at the beginning if no system message\n          context.unshift(assistantMsg);\n        }\n      }\n    }\n  }\n  }\n\n  const prunedMemory = messages;\n  summaryIndex = prunedMemory.length - 1;\n  remainingContextTokens -= currentTokenCount;\n\n  return {\n    summaryIndex,\n    remainingContextTokens,\n    context: context.reverse(),\n    messagesToRefine: prunedMemory,\n  };\n}\n\nfunction checkValidNumber(value: unknown): value is number {\n  return typeof value === 'number' && !isNaN(value) && value > 0;\n}\n\nexport function createPruneMessages(factoryParams: PruneMessagesFactoryParams) {\n  const indexTokenCountMap = { ...factoryParams.indexTokenCountMap };\n  let lastTurnStartIndex = factoryParams.startIndex;\n  let totalTokens = (Object.values(indexTokenCountMap)).reduce((a, b) => a + b, 0);\n  \n  return function pruneMessages(params: PruneMessagesParams): {\n    context: BaseMessage[];\n    indexTokenCountMap: Record<string, number>;\n  } {\n    let currentUsage: UsageMetadata | undefined;\n    if (params.usageMetadata && (\n      checkValidNumber(params.usageMetadata.input_tokens)\n      || (\n        checkValidNumber(params.usageMetadata.input_token_details)\n        && (\n          checkValidNumber(params.usageMetadata.input_token_details.cache_creation)\n          || checkValidNumber(params.usageMetadata.input_token_details.cache_read)\n        )\n      )\n    ) && checkValidNumber(params.usageMetadata.output_tokens)) {\n      currentUsage = calculateTotalTokens(params.usageMetadata);\n      totalTokens = currentUsage.total_tokens;\n    }\n\n    for (let i = lastTurnStartIndex; i < params.messages.length; i++) {\n      const message = params.messages[i];\n      if (i === lastTurnStartIndex && indexTokenCountMap[i] === undefined && currentUsage) {\n        indexTokenCountMap[i] = currentUsage.output_tokens;\n      } else if (indexTokenCountMap[i] === undefined) {\n        indexTokenCountMap[i] = factoryParams.tokenCounter(message);\n        totalTokens += indexTokenCountMap[i];\n      }\n    }\n\n    // If `currentUsage` is defined, we need to distribute the current total tokensto our `indexTokenCountMap`,\n    // for all message index keys before `lastTurnStartIndex`, as it has the most accurate count for those messages.\n    // We must distribute it in a weighted manner, so that the total token count is equal to `currentUsage.total_tokens`,\n    // relative the manually counted tokens in `indexTokenCountMap`.\n    if (currentUsage) {\n      const totalIndexTokens = Object.values(indexTokenCountMap).reduce((a, b) => a + b, 0);\n      const ratio = currentUsage.total_tokens / totalIndexTokens;\n      for (const key in indexTokenCountMap) {\n        indexTokenCountMap[key] = Math.round(indexTokenCountMap[key] * ratio);\n      }\n    }\n\n    lastTurnStartIndex = params.messages.length;\n    if (totalTokens <= factoryParams.maxTokens) {\n      return { context: params.messages, indexTokenCountMap };\n    }\n\n    // Pass the tokenCounter to getMessagesWithinTokenLimit for token recalculation\n    const { context } = getMessagesWithinTokenLimit({\n      maxContextTokens: factoryParams.maxTokens,\n      messages: params.messages,\n      indexTokenCountMap,\n      startOnMessageType: params.startOnMessageType,\n      thinkingEnabled: factoryParams.thinkingEnabled,\n      tokenCounter: factoryParams.tokenCounter,\n    });\n\n    return { context, indexTokenCountMap };\n  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+{"version":3,"file":"prune.mjs","sources":["../../../src/messages/prune.ts"],"sourcesContent":["import { AIMessage } from '@langchain/core/messages';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { TokenCounter } from '@/types/run';\nexport type PruneMessagesFactoryParams = {\n  maxTokens: number;\n  startIndex: number;\n  tokenCounter: TokenCounter;\n  indexTokenCountMap: Record<string, number>;\n  thinkingEnabled?: boolean;\n};\nexport type PruneMessagesParams = {\n  messages: BaseMessage[];\n  usageMetadata?: Partial<UsageMetadata>;\n  startOnMessageType?: ReturnType<BaseMessage['getType']>;\n}\n\n/**\n * Calculates the total tokens from a single usage object\n * \n * @param usage The usage metadata object containing token information\n * @returns An object containing the total input and output tokens\n */\nfunction calculateTotalTokens(usage: Partial<UsageMetadata>): UsageMetadata {\n  const baseInputTokens = Number(usage.input_tokens) || 0;\n  const cacheCreation = Number(usage.input_token_details?.cache_creation) || 0;\n  const cacheRead = Number(usage.input_token_details?.cache_read) || 0;\n  \n  const totalInputTokens = baseInputTokens + cacheCreation + cacheRead;\n  const totalOutputTokens = Number(usage.output_tokens) || 0;\n\n  return {\n    input_tokens: totalInputTokens,\n    output_tokens: totalOutputTokens,\n    total_tokens: totalInputTokens + totalOutputTokens\n  };\n}\n\n/**\n * Processes an array of messages and returns a context of messages that fit within a specified token limit.\n * It iterates over the messages from newest to oldest, adding them to the context until the token limit is reached.\n * \n * @param options Configuration options for processing messages\n * @returns Object containing the message context, remaining tokens, messages not included, and summary index\n */\nfunction getMessagesWithinTokenLimit({\n  messages: _messages,\n  maxContextTokens,\n  indexTokenCountMap,\n  startOnMessageType,\n  thinkingEnabled,\n  tokenCounter,\n}: {\n  messages: BaseMessage[];\n  maxContextTokens: number;\n  indexTokenCountMap: Record<string, number>;\n  startOnMessageType?: string;\n  thinkingEnabled?: boolean;\n  tokenCounter?: TokenCounter;\n}): {\n  context: BaseMessage[];\n  remainingContextTokens: number;\n  messagesToRefine: BaseMessage[];\n  summaryIndex: number;\n} {\n  // Every reply is primed with <|start|>assistant<|message|>, so we\n  // start with 3 tokens for the label after all messages have been counted.\n  let summaryIndex = -1;\n  let currentTokenCount = 3;\n  const instructions = _messages?.[0]?.getType() === 'system' ? _messages[0] : undefined;\n  const instructionsTokenCount = instructions != null ? indexTokenCountMap[0] : 0;\n  let remainingContextTokens = maxContextTokens - instructionsTokenCount;\n  const messages = [..._messages];\n  let context: BaseMessage[] = [];\n\n  if (currentTokenCount < remainingContextTokens) {\n    let currentIndex = messages.length;\n    while (messages.length > 0 && currentTokenCount < remainingContextTokens && currentIndex > 1) {\n      currentIndex--;\n      if (messages.length === 1 && instructions) {\n        break;\n      }\n      const poppedMessage = messages.pop();\n      if (!poppedMessage) continue;\n      \n      const tokenCount = indexTokenCountMap[currentIndex] || 0;\n\n      if ((currentTokenCount + tokenCount) <= remainingContextTokens) {\n        context.push(poppedMessage);\n        currentTokenCount += tokenCount;\n      } else {\n        messages.push(poppedMessage);\n        break;\n      }\n    }\n    \n  // Handle startOnMessageType requirement\n  if (startOnMessageType && context.length > 0) {\n    const requiredTypeIndex = context.findIndex(msg => msg.getType() === startOnMessageType);\n    \n    if (requiredTypeIndex > 0) {\n      context = context.slice(requiredTypeIndex);\n    }\n  }\n  \n  // Add system message if it exists\n  if (instructions && _messages.length > 0) {\n    context.push(_messages[0] as BaseMessage);\n    messages.shift();\n  }\n  \n  // Handle thinking mode requirement for Anthropic\n  if (thinkingEnabled && context.length > 0 && tokenCounter) {\n    // Check if the latest message is an assistant message\n    const latestMessageIsAssistant = _messages.length > 0 && _messages[_messages.length - 1].getType() === 'ai';\n    \n    // Process only if we have an assistant message in the context\n    const firstAssistantIndex = context.findIndex(msg => msg.getType() === 'ai');\n    \n    if (firstAssistantIndex >= 0) {\n      const firstAssistantMsg = context[firstAssistantIndex];\n      \n      // Check if the first assistant message already has a thinking block\n      const hasThinkingBlock = Array.isArray(firstAssistantMsg.content) && \n        firstAssistantMsg.content.some(item => \n          item && typeof item === 'object' && item.type === 'thinking');\n      \n      // Only proceed if we need to add thinking blocks\n      if (!hasThinkingBlock) {\n        // Collect thinking blocks from pruned assistant messages, starting from the most recent\n        const thinkingBlocks: any[] = [];\n        \n        // Look through pruned messages for thinking blocks, starting from the end (most recent)\n        for (let i = messages.length - 1; i >= 0; i--) {\n          const msg = messages[i];\n          if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n            for (const item of msg.content) {\n              if (item && typeof item === 'object' && item.type === 'thinking') {\n                thinkingBlocks.push(item);\n                // We only need one thinking block\n                break;\n              }\n            }\n            if (thinkingBlocks.length > 0) break; // Stop after finding one thinking block\n          }\n        }\n        \n        // If we found thinking blocks, add them to the first assistant message\n        if (thinkingBlocks.length > 0) {\n          // Calculate token count of original message\n          const originalTokenCount = tokenCounter(firstAssistantMsg);\n          \n          // Create a new content array with thinking blocks at the beginning\n          let newContent: any[];\n          \n          if (Array.isArray(firstAssistantMsg.content)) {\n            // Keep the original content (excluding any existing thinking blocks)\n            const originalContent = firstAssistantMsg.content.filter(item => \n              !(item && typeof item === 'object' && item.type === 'thinking'));\n            \n            newContent = [...thinkingBlocks, ...originalContent];\n          } else if (typeof firstAssistantMsg.content === 'string') {\n            newContent = [\n              ...thinkingBlocks,\n              { type: 'text', text: firstAssistantMsg.content }\n            ];\n          } else {\n            newContent = thinkingBlocks;\n          }\n          \n          // Create a new message with the updated content\n          const newMessage = new AIMessage({\n            content: newContent,\n            additional_kwargs: firstAssistantMsg.additional_kwargs,\n            response_metadata: firstAssistantMsg.response_metadata,\n          });\n          \n          // Calculate token count of new message\n          const newTokenCount = tokenCounter(newMessage);\n          \n          // Adjust current token count\n          currentTokenCount += (newTokenCount - originalTokenCount);\n          \n          // Replace the first assistant message\n          context[firstAssistantIndex] = newMessage;\n          \n          // If we've exceeded the token limit, we need to prune more messages\n          if (currentTokenCount > remainingContextTokens) {\n            // Build a map of tool call IDs to track AI <--> tool message correspondences\n            const toolCallIdMap = new Map<string, number>();\n            \n            // Identify tool call IDs in the context\n            for (let i = 0; i < context.length; i++) {\n              const msg = context[i];\n              \n              // Check for tool calls in AI messages\n              if (msg.getType() === 'ai' && Array.isArray(msg.content)) {\n                for (const item of msg.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    toolCallIdMap.set(item.id, i);\n                  }\n                }\n              }\n              \n              // Check for tool messages\n              if (msg.getType() === 'tool' && 'tool_call_id' in msg && typeof msg.tool_call_id === 'string') {\n                toolCallIdMap.set(msg.tool_call_id, i);\n              }\n            }\n            \n            // Track which messages to remove\n            const indicesToRemove = new Set<number>();\n            \n            // Start removing messages from the end, but preserve AI <--> tool message correspondences\n            let i = context.length - 1;\n            while (i > firstAssistantIndex && currentTokenCount > remainingContextTokens) {\n              const msgToRemove = context[i];\n              \n              // Check if this is a tool message or has tool calls\n              let canRemove = true;\n              \n              if (msgToRemove.getType() === 'tool' && 'tool_call_id' in msgToRemove && typeof msgToRemove.tool_call_id === 'string') {\n                // If this is a tool message, check if we need to keep its corresponding AI message\n                const aiIndex = toolCallIdMap.get(msgToRemove.tool_call_id);\n                if (aiIndex !== undefined && aiIndex !== i && !indicesToRemove.has(aiIndex)) {\n                  // We need to remove both the tool message and its corresponding AI message\n                  indicesToRemove.add(i);\n                  indicesToRemove.add(aiIndex);\n                  currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[aiIndex]));\n                  canRemove = false;\n                }\n              } else if (msgToRemove.getType() === 'ai' && Array.isArray(msgToRemove.content)) {\n                // If this is an AI message with tool calls, check if we need to keep its corresponding tool messages\n                for (const item of msgToRemove.content) {\n                  if (item && typeof item === 'object' && item.type === 'tool_use' && item.id) {\n                    const toolIndex = toolCallIdMap.get(item.id as string);\n                    if (toolIndex !== undefined && toolIndex !== i && !indicesToRemove.has(toolIndex)) {\n                      // We need to remove both the AI message and its corresponding tool message\n                      indicesToRemove.add(i);\n                      indicesToRemove.add(toolIndex);\n                      currentTokenCount -= (tokenCounter(msgToRemove) + tokenCounter(context[toolIndex]));\n                      canRemove = false;\n                      break;\n                    }\n                  }\n                }\n              }\n              \n              // If we can remove this message individually\n              if (canRemove && !indicesToRemove.has(i)) {\n                indicesToRemove.add(i);\n                currentTokenCount -= tokenCounter(msgToRemove);\n              }\n              \n              i--;\n            }\n            \n            // Remove messages in reverse order to avoid index shifting\n            const sortedIndices = Array.from(indicesToRemove).sort((a, b) => b - a);\n            for (const index of sortedIndices) {\n              context.splice(index, 1);\n            }\n            \n            // Update remainingContextTokens to reflect the new token count\n            remainingContextTokens = maxContextTokens - currentTokenCount;\n          }\n        }\n      }\n    }\n    \n    // If the latest message is an assistant message, ensure an assistant message with thinking appears at the end\n    // of the context (which will become the beginning after reversal)\n    // but maintain system message precedence after reversal\n    if (latestMessageIsAssistant && context.length > 0) {\n      // Find assistant messages with thinking blocks\n      const assistantIndices: number[] = [];\n      for (let i = 0; i < context.length; i++) {\n        const msg = context[i];\n        if (msg.getType() === 'ai') {\n          const hasThinking = Array.isArray(msg.content) && \n            msg.content.some(item => item && typeof item === 'object' && item.type === 'thinking');\n          \n          if (hasThinking) {\n            assistantIndices.push(i);\n          }\n        }\n      }\n      \n      // If we found assistant messages with thinking blocks\n      if (assistantIndices.length > 0) {\n        // Get the first assistant message with thinking\n        const assistantWithThinkingIndex = assistantIndices[0];\n        const assistantWithThinking = context[assistantWithThinkingIndex];\n        \n        // Remove it from its current position\n        context.splice(assistantWithThinkingIndex, 1);\n        \n        // Check if there's a system message in the context\n        const systemIndex = context.findIndex(msg => msg.getType() === 'system');\n        const hasSystem = systemIndex !== -1;\n        \n        if (hasSystem) {\n          // We want the system message to be first after reversal\n          // This means we need to put it at the end position before reversal\n          // And the assistant message should be second after reversal\n          // This means we need to put it at the end - 1 position before reversal\n          \n          // First, ensure the system message is at the end (will be first after reversal)\n          const systemMsg = context[systemIndex];\n          context.splice(systemIndex, 1);\n          context.push(systemMsg);\n          \n          // Then, put the assistant message right before the system message (will be second after reversal)\n          context.splice(context.length - 1, 0, assistantWithThinking);\n        } else {\n          // No system message, so we want assistant to be first after reversal\n          // This means we need to put it at the end position before reversal\n          context.push(assistantWithThinking);\n        }\n      }\n    }\n  }\n  }\n\n  const prunedMemory = messages;\n  summaryIndex = prunedMemory.length - 1;\n  remainingContextTokens -= currentTokenCount;\n\n  return {\n    summaryIndex,\n    remainingContextTokens,\n    context: context.reverse(),\n    messagesToRefine: prunedMemory,\n  };\n}\n\nfunction checkValidNumber(value: unknown): value is number {\n  return typeof value === 'number' && !isNaN(value) && value > 0;\n}\n\nexport function createPruneMessages(factoryParams: PruneMessagesFactoryParams) {\n  const indexTokenCountMap = { ...factoryParams.indexTokenCountMap };\n  let lastTurnStartIndex = factoryParams.startIndex;\n  let totalTokens = (Object.values(indexTokenCountMap)).reduce((a, b) => a + b, 0);\n  \n  return function pruneMessages(params: PruneMessagesParams): {\n    context: BaseMessage[];\n    indexTokenCountMap: Record<string, number>;\n  } {\n    let currentUsage: UsageMetadata | undefined;\n    if (params.usageMetadata && (\n      checkValidNumber(params.usageMetadata.input_tokens)\n      || (\n        checkValidNumber(params.usageMetadata.input_token_details)\n        && (\n          checkValidNumber(params.usageMetadata.input_token_details.cache_creation)\n          || checkValidNumber(params.usageMetadata.input_token_details.cache_read)\n        )\n      )\n    ) && checkValidNumber(params.usageMetadata.output_tokens)) {\n      currentUsage = calculateTotalTokens(params.usageMetadata);\n      totalTokens = currentUsage.total_tokens;\n    }\n\n    for (let i = lastTurnStartIndex; i < params.messages.length; i++) {\n      const message = params.messages[i];\n      if (i === lastTurnStartIndex && indexTokenCountMap[i] === undefined && currentUsage) {\n        indexTokenCountMap[i] = currentUsage.output_tokens;\n      } else if (indexTokenCountMap[i] === undefined) {\n        indexTokenCountMap[i] = factoryParams.tokenCounter(message);\n        totalTokens += indexTokenCountMap[i];\n      }\n    }\n\n    // If `currentUsage` is defined, we need to distribute the current total tokensto our `indexTokenCountMap`,\n    // for all message index keys before `lastTurnStartIndex`, as it has the most accurate count for those messages.\n    // We must distribute it in a weighted manner, so that the total token count is equal to `currentUsage.total_tokens`,\n    // relative the manually counted tokens in `indexTokenCountMap`.\n    if (currentUsage) {\n      const totalIndexTokens = Object.values(indexTokenCountMap).reduce((a, b) => a + b, 0);\n      const ratio = currentUsage.total_tokens / totalIndexTokens;\n      for (const key in indexTokenCountMap) {\n        indexTokenCountMap[key] = Math.round(indexTokenCountMap[key] * ratio);\n      }\n    }\n\n    lastTurnStartIndex = params.messages.length;\n    if (totalTokens <= factoryParams.maxTokens) {\n      return { context: params.messages, indexTokenCountMap };\n    }\n\n    // Pass the tokenCounter to getMessagesWithinTokenLimit for token recalculation\n    const { context } = getMessagesWithinTokenLimit({\n      maxContextTokens: factoryParams.maxTokens,\n      messages: params.messages,\n      indexTokenCountMap,\n      startOnMessageType: params.startOnMessageType,\n      thinkingEnabled: factoryParams.thinkingEnabled,\n      tokenCounter: factoryParams.tokenCounter,\n    });\n\n    return { context, indexTokenCountMap };\n  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package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@librechat/agents",
-  "version": "2.3.0",
+  "version": "2.3.1",
   "main": "./dist/cjs/main.cjs",
   "module": "./dist/esm/main.mjs",
   "types": "./dist/types/index.d.ts",

package/src/messages/prune.ts

@@ -267,25 +267,54 @@ function getMessagesWithinTokenLimit({
       }
     }
     
-    // If the latest message is an assistant message, ensure an assistant message appears early in the context
-    // but maintain system message precedence
+    // If the latest message is an assistant message, ensure an assistant message with thinking appears at the end
+    // of the context (which will become the beginning after reversal)
+    // but maintain system message precedence after reversal
     if (latestMessageIsAssistant && context.length > 0) {
-      // Find the first assistant message in the context
-      const assistantIndex = context.findIndex(msg => msg.getType() === 'ai');
-      if (assistantIndex > 0) {
-        // Check if there's a system message at the beginning
-        const hasSystemFirst = context[0].getType() === 'system';
+      // Find assistant messages with thinking blocks
+      const assistantIndices: number[] = [];
+      for (let i = 0; i < context.length; i++) {
+        const msg = context[i];
+        if (msg.getType() === 'ai') {
+          const hasThinking = Array.isArray(msg.content) && 
+            msg.content.some(item => item && typeof item === 'object' && item.type === 'thinking');
+          
+          if (hasThinking) {
+            assistantIndices.push(i);
+          }
+        }
+      }
+      
+      // If we found assistant messages with thinking blocks
+      if (assistantIndices.length > 0) {
+        // Get the first assistant message with thinking
+        const assistantWithThinkingIndex = assistantIndices[0];
+        const assistantWithThinking = context[assistantWithThinkingIndex];
+        
+        // Remove it from its current position
+        context.splice(assistantWithThinkingIndex, 1);
         
-        // Move the assistant message to the appropriate position
-        const assistantMsg = context[assistantIndex];
-        context.splice(assistantIndex, 1);
+        // Check if there's a system message in the context
+        const systemIndex = context.findIndex(msg => msg.getType() === 'system');
+        const hasSystem = systemIndex !== -1;
         
-        if (hasSystemFirst) {
-          // Insert after the system message
-          context.splice(1, 0, assistantMsg);
+        if (hasSystem) {
+          // We want the system message to be first after reversal
+          // This means we need to put it at the end position before reversal
+          // And the assistant message should be second after reversal
+          // This means we need to put it at the end - 1 position before reversal
+          
+          // First, ensure the system message is at the end (will be first after reversal)
+          const systemMsg = context[systemIndex];
+          context.splice(systemIndex, 1);
+          context.push(systemMsg);
+          
+          // Then, put the assistant message right before the system message (will be second after reversal)
+          context.splice(context.length - 1, 0, assistantWithThinking);
         } else {
-          // Insert at the beginning if no system message
-          context.unshift(assistantMsg);
+          // No system message, so we want assistant to be first after reversal
+          // This means we need to put it at the end position before reversal
+          context.push(assistantWithThinking);
         }
       }
     }

package/src/specs/thinking-prune.test.ts

@@ -498,11 +498,11 @@ describe('Prune Messages with Thinking Mode Tests', () => {
     }
   });
   
-  it('should ensure an assistant message appears early in the context when the latest message is an assistant message', () => {
+  it('should ensure an assistant message with thinking appears at the beginning of the context when the latest message is an assistant message', () => {
     // Create a token counter
     const tokenCounter = createTestTokenCounter();
     
-    // Create messages with the latest message being an assistant message
+    // Create messages with the latest message being an assistant message with thinking
     const assistantMessageWithThinking = new AIMessage({
       content: [
         {
@@ -516,12 +516,41 @@ describe('Prune Messages with Thinking Mode Tests', () => {
       ],
     });
     
+    // Create an assistant message with tool use
+    const assistantMessageWithToolUse = new AIMessage({
+      content: [
+        {
+          type: "text",
+          text: "Let me check that file:",
+        },
+        {
+          type: "tool_use",
+          id: "tool123",
+          name: "text_editor_mcp_textEditor",
+          input: "{\"command\": \"view\", \"path\": \"/path/to/file.txt\"}",
+        },
+      ],
+    });
+    
+    // Create a tool response message
+    const toolResponseMessage = new ToolMessage({
+      content: [
+        {
+          type: "text",
+          text: "{\"success\":true,\"message\":\"File content\"}",
+        },
+      ],
+      tool_call_id: "tool123",
+      name: "text_editor_mcp_textEditor",
+    });
+    
     // Test case without system message
     const messagesWithoutSystem = [
       new HumanMessage("Hello"),
-      new AIMessage("First assistant response"),
+      assistantMessageWithToolUse,
+      toolResponseMessage,
       new HumanMessage("Next message"),
-      assistantMessageWithThinking, // Latest message is an assistant message
+      assistantMessageWithThinking, // Latest message is an assistant message with thinking
     ];
     
     // Calculate token counts for each message
@@ -532,7 +561,7 @@ describe('Prune Messages with Thinking Mode Tests', () => {
     
     // Create pruneMessages function with thinking mode enabled
     const pruneMessagesWithoutSystem = createPruneMessages({
-      maxTokens: 60, // Set a lower token limit to force more pruning
+      maxTokens: 100, // Set a token limit to force some pruning
       startIndex: 0,
       tokenCounter,
       indexTokenCountMap: { ...indexTokenCountMapWithoutSystem },
@@ -542,17 +571,25 @@ describe('Prune Messages with Thinking Mode Tests', () => {
     // Prune messages
     const resultWithoutSystem = pruneMessagesWithoutSystem({ messages: messagesWithoutSystem });
     
-    // Verify that the first message in the pruned context is an assistant message when no system message
+    // Verify that the first message in the pruned context is an assistant message with thinking when no system message
     expect(resultWithoutSystem.context.length).toBeGreaterThan(0);
     expect(resultWithoutSystem.context[0].getType()).toBe('ai');
     
+    // Verify that the first message has a thinking block
+    const firstMsgContent = resultWithoutSystem.context[0].content as any[];
+    expect(Array.isArray(firstMsgContent)).toBe(true);
+    const hasThinkingBlock = firstMsgContent.some(item => 
+      item && typeof item === 'object' && item.type === 'thinking');
+    expect(hasThinkingBlock).toBe(true);
+    
     // Test case with system message
     const messagesWithSystem = [
       new SystemMessage("System instruction"),
       new HumanMessage("Hello"),
-      new AIMessage("First assistant response"),
+      assistantMessageWithToolUse,
+      toolResponseMessage,
       new HumanMessage("Next message"),
-      assistantMessageWithThinking, // Latest message is an assistant message
+      assistantMessageWithThinking, // Latest message is an assistant message with thinking
     ];
     
     // Calculate token counts for each message
@@ -563,7 +600,7 @@ describe('Prune Messages with Thinking Mode Tests', () => {
     
     // Create pruneMessages function with thinking mode enabled
     const pruneMessagesWithSystem = createPruneMessages({
-      maxTokens: 70, // Set a token limit to force some pruning but keep system message
+      maxTokens: 120, // Set a token limit to force some pruning but keep system message
       startIndex: 0,
       tokenCounter,
       indexTokenCountMap: { ...indexTokenCountMapWithSystem },
@@ -573,10 +610,17 @@ describe('Prune Messages with Thinking Mode Tests', () => {
     // Prune messages
     const resultWithSystem = pruneMessagesWithSystem({ messages: messagesWithSystem });
     
-    // Verify that the system message remains first, followed by an assistant message
+    // Verify that the system message remains first, followed by an assistant message with thinking
     expect(resultWithSystem.context.length).toBeGreaterThan(1);
     expect(resultWithSystem.context[0].getType()).toBe('system');
     expect(resultWithSystem.context[1].getType()).toBe('ai');
+    
+    // Verify that the second message has a thinking block
+    const secondMsgContent = resultWithSystem.context[1].content as any[];
+    expect(Array.isArray(secondMsgContent)).toBe(true);
+    const hasThinkingBlockInSecond = secondMsgContent.some(item => 
+      item && typeof item === 'object' && item.type === 'thinking');
+    expect(hasThinkingBlockInSecond).toBe(true);
   });
   
   it('should look for thinking blocks starting from the most recent messages', () => {