@roj-ai/sdk 0.1.20 → 0.1.21

package/dist/plugins/limits-guard/plugin.js

@@ -1,20 +1,34 @@
 import { agentEvents } from '../../core/agents/state.js';
+import { contextEvents } from '../../core/context/state.js';
 import { llmEvents } from '../../core/llm/state.js';
 import { definePlugin } from '../../core/plugins/plugin-builder.js';
 import { selectPluginState } from '../../core/sessions/reducer.js';
 import { toolEvents } from '../../core/tools/state.js';
 import { responseFingerprint, toolCallFingerprint } from '../../lib/utils/hash.js';
 import { mailboxEvents } from '../../plugins/mailbox/state.js';
-import { checkLimits, countConsecutiveTailDuplicates, resolveAgentLimits } from './limit-guard.js';
+import { checkBudget, checkLimits, countConsecutiveTailDuplicates, resolveAgentLimits, resolveSessionLimits, } from './limit-guard.js';
 export const createAgentCounters = () => ({
     inferenceCount: 0,
     toolCallCount: 0,
     spawnedAgentCount: 0,
     messagesSentCount: 0,
+    compactionCount: 0,
+    costSpent: 0,
+    tokensUsed: 0,
     consecutiveToolFailures: {},
     recentToolCallHashes: [],
     recentResponseHashes: [],
 });
+/** Sum cost + tokens across all agents in the session (for the session-wide budget). */
+export function sumSessionSpend(limits) {
+    let costSpent = 0;
+    let tokensUsed = 0;
+    for (const counters of limits.values()) {
+        costSpent += counters.costSpent;
+        tokensUsed += counters.tokensUsed;
+    }
+    return { costSpent, tokensUsed };
+}
 /**
  * Extract agent counters from session state (for external consumers).
  */
@@ -36,6 +50,16 @@ export const limitsEvents = createEventsFactory({
             hardLimit: z.number(),
             message: z.string(),
         }),
+        budget_exceeded: z.object({
+            agentId: agentIdSchema,
+            /** Whether the per-agent or the session-wide budget was hit. */
+            scope: z.enum(['agent', 'session']),
+            /** Which limit tripped: maxCost / maxTokens / maxSessionCost / maxSessionTokens. */
+            limitName: z.string(),
+            spent: z.number(),
+            limit: z.number(),
+            message: z.string(),
+        }),
     },
 });
 // ============================================================================
@@ -54,7 +78,8 @@ function resolveToolName(sessionState, agentId, toolCallId) {
         ?? 'unknown';
 }
 export const limitsGuardPlugin = definePlugin('limits-guard')
-    .events([agentEvents, llmEvents, toolEvents, mailboxEvents])
+    .events([agentEvents, llmEvents, toolEvents, mailboxEvents, contextEvents, limitsEvents])
+    .pluginConfig()
     .state({
     key: 'agentLimits',
     initial: () => new Map(),
@@ -109,10 +134,38 @@ export const limitsGuardPlugin = definePlugin('limits-guard')
                 newLimits.set(event.agentId, {
                     ...counters,
                     inferenceCount: counters.inferenceCount + 1,
+                    costSpent: counters.costSpent + (event.metrics.cost ?? 0),
+                    tokensUsed: counters.tokensUsed + (event.metrics.totalTokens ?? 0),
                     recentResponseHashes: newRecentResponseHashes,
                 });
                 return newLimits;
             }
+            case 'auxiliary_inference_completed': {
+                // Side-channel calls (e.g. context compaction) are billed but don't
+                // touch conversation state, so they count toward cost/token budgets
+                // but NOT toward inferenceCount or the anti-looping response hashes.
+                const counters = limits.get(event.agentId);
+                if (!counters)
+                    return limits;
+                const newLimits = new Map(limits);
+                newLimits.set(event.agentId, {
+                    ...counters,
+                    costSpent: counters.costSpent + (event.metrics.cost ?? 0),
+                    tokensUsed: counters.tokensUsed + (event.metrics.totalTokens ?? 0),
+                });
+                return newLimits;
+            }
+            case 'context_compacted': {
+                const counters = limits.get(event.agentId);
+                if (!counters)
+                    return limits;
+                const newLimits = new Map(limits);
+                newLimits.set(event.agentId, {
+                    ...counters,
+                    compactionCount: counters.compactionCount + 1,
+                });
+                return newLimits;
+            }
             case 'tool_started': {
                 const counters = limits.get(event.agentId);
                 if (!counters)
@@ -161,6 +214,11 @@ export const limitsGuardPlugin = definePlugin('limits-guard')
                 const counters = limits.get(event.agentId);
                 if (!counters)
                     return limits;
+                // Reset the anti-looping counters so the agent can make progress
+                // again. Budget spend (costSpent/tokensUsed) is deliberately NOT
+                // reset — otherwise a per-agent or session cost cap could be bypassed
+                // by repeatedly pausing and resuming. To grant more budget, raise the
+                // configured limit instead.
                 const newLimits = new Map(limits);
                 newLimits.set(event.agentId, {
                     ...counters,
@@ -168,6 +226,7 @@ export const limitsGuardPlugin = definePlugin('limits-guard')
                     toolCallCount: 0,
                     spawnedAgentCount: 0,
                     messagesSentCount: 0,
+                    compactionCount: 0,
                     consecutiveToolFailures: {},
                     recentToolCallHashes: [],
                     recentResponseHashes: [],
@@ -180,6 +239,42 @@ export const limitsGuardPlugin = definePlugin('limits-guard')
     },
 })
     .agentConfig()
+    .hook('beforeInference', async (ctx) => {
+    // Budgets are enforced here (before the call) so an exhausted agent is
+    // paused before spending more — cost/tokens of a call aren't known until
+    // after it returns, so we stop the *next* call once the threshold is hit.
+    const counters = ctx.pluginState.get(ctx.agentId);
+    if (!counters)
+        return null;
+    const agentLimits = resolveAgentLimits(ctx.pluginAgentConfig?.limits);
+    const agentCheck = checkBudget(counters, agentLimits.maxCost, agentLimits.maxTokens, agentLimits.softLimitRatio, { cost: 'maxCost', tokens: 'maxTokens' });
+    if (agentCheck.status === 'hard_limit') {
+        await ctx.emitEvent(limitsEvents.create('budget_exceeded', {
+            agentId: ctx.agentId,
+            scope: 'agent',
+            limitName: agentCheck.limitName,
+            spent: agentCheck.currentValue,
+            limit: agentCheck.hardLimit,
+            message: agentCheck.reason,
+        }));
+        return { action: 'pause', reason: `Agent budget exceeded — ${agentCheck.reason}` };
+    }
+    const sessionLimits = resolveSessionLimits(ctx.pluginConfig);
+    const sessionSpend = sumSessionSpend(ctx.pluginState);
+    const sessionCheck = checkBudget(sessionSpend, sessionLimits.maxSessionCost, sessionLimits.maxSessionTokens, sessionLimits.softLimitRatio, { cost: 'maxSessionCost', tokens: 'maxSessionTokens' });
+    if (sessionCheck.status === 'hard_limit') {
+        await ctx.emitEvent(limitsEvents.create('budget_exceeded', {
+            agentId: ctx.agentId,
+            scope: 'session',
+            limitName: sessionCheck.limitName,
+            spent: sessionCheck.currentValue,
+            limit: sessionCheck.hardLimit,
+            message: sessionCheck.reason,
+        }));
+        return { action: 'pause', reason: `Session budget exceeded — ${sessionCheck.reason}` };
+    }
+    return null;
+})
     .hook('afterInference', async (ctx) => {
     const resolvedLimits = resolveAgentLimits(ctx.pluginAgentConfig?.limits);
     const counters = ctx.pluginState.get(ctx.agentId);
@@ -234,6 +329,16 @@ export const limitsGuardPlugin = definePlugin('limits-guard')
         parts.push(`⚠️ Approaching ${limitCheck.limitName} limit: ${limitCheck.currentValue}/${limitCheck.hardLimit}. `
             + `Wrap up your current task or you will be stopped.`);
     }
+    // Budget soft warnings — per-agent spend, then the session-wide budget.
+    const agentBudget = checkBudget(counters, resolvedLimits.maxCost, resolvedLimits.maxTokens, resolvedLimits.softLimitRatio, { cost: 'maxCost', tokens: 'maxTokens' });
+    if (agentBudget.status === 'soft_warning') {
+        parts.push(`⚠️ ${agentBudget.message}. You will be paused when the budget is reached — wrap up.`);
+    }
+    const sessionLimits = resolveSessionLimits(ctx.pluginConfig);
+    const sessionBudget = checkBudget(sumSessionSpend(ctx.pluginState), sessionLimits.maxSessionCost, sessionLimits.maxSessionTokens, sessionLimits.softLimitRatio, { cost: 'maxSessionCost', tokens: 'maxSessionTokens' });
+    if (sessionBudget.status === 'soft_warning') {
+        parts.push(`⚠️ Session-wide ${sessionBudget.message}.`);
+    }
     return parts.length > 0 ? parts.join('\n\n') : null;
 })
     .build();

package/dist/plugins/limits-guard/plugin.js.map

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package/dist/plugins/mailbox/plugin.d.ts.map

@@ -1 +1 @@
-{"version":3,"file":"plugin.d.ts","sourceRoot":"","sources":["../../../src/plugins/mailbox/plugin.ts"],"names":[],"mappings":"AAAA;;;;;;GAMG;AAEH,OAAO,CAAC,MAAM,QAAQ,CAAC;AAyBvB;;GAEG;AACH,MAAM,MAAM,mBAAmB,GAAG,EAAE,CAAC;AAErC;;GAEG;AACH,MAAM,WAAW,kBAAkB;IAClC,wFAAwF;IACxF,qBAAqB,CAAC,EAAE,OAAO,CAAC;CAChC;AAED,eAAO,MAAM,aAAa;;;;;;;;;;;GAmPjB,CAAC"}
+{"version":3,"file":"plugin.d.ts","sourceRoot":"","sources":["../../../src/plugins/mailbox/plugin.ts"],"names":[],"mappings":"AAAA;;;;;;GAMG;AAEH,OAAO,CAAC,MAAM,QAAQ,CAAC;AAyBvB;;GAEG;AACH,MAAM,MAAM,mBAAmB,GAAG,EAAE,CAAC;AAErC;;GAEG;AACH,MAAM,WAAW,kBAAkB;IAClC,wFAAwF;IACxF,qBAAqB,CAAC,EAAE,OAAO,CAAC;CAChC;AAED,eAAO,MAAM,aAAa;;;;;;;;;;;GAqQjB,CAAC"}

package/dist/plugins/mailbox/plugin.js

@@ -167,6 +167,24 @@ export const mailboxPlugin = definePlugin("mailbox")
         content: `Agent encountered an error: ${ctx.error}`,
     });
     return null;
+})
+    .hook("onPause", async (ctx) => {
+    // Notify the parent immediately when a child pauses (budget/limit exhaustion,
+    // manual pause, …) so it can react: resume after addressing the cause,
+    // reassign the work, or stop. Lives here (not in the agents plugin) because
+    // the agents plugin is disabled on leaf agents that can't spawn — but those
+    // are exactly the agents that pause and need to report upward. mailbox is
+    // enabled on every agent, and self.send wakes the parent. Root agents
+    // (no parent) have no one to notify.
+    const parentId = ctx.agentState.parentId;
+    if (!parentId || !ctx.sessionState.agents.has(parentId))
+        return null;
+    await ctx.self.send({
+        fromAgentId: ctx.agentId,
+        toAgentId: parentId,
+        content: `<child-paused agent="${ctx.agentId}">${ctx.reason ?? "no reason given"}</child-paused>`,
+    });
+    return null;
 })
     .systemPrompt((ctx) => {
     const role = getAgentRole(ctx.agentState, ctx.sessionState);

package/dist/plugins/mailbox/plugin.js.map

@@ -1 +1 @@
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package/dist/plugins/session-stats/plugin.d.ts.map

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+{"version":3,"file":"plugin.d.ts","sourceRoot":"","sources":["../../../src/plugins/session-stats/plugin.ts"],"names":[],"mappings":"AAIA,OAAO,KAAK,EAAE,YAAY,EAAE,MAAM,0BAA0B,CAAA;AAO5D,MAAM,WAAW,aAAa;IAC7B,QAAQ,EAAE,MAAM,CAAA;IAChB,WAAW,EAAE,MAAM,CAAA;IACnB,YAAY,EAAE,MAAM,CAAA;IACpB,gBAAgB,EAAE,MAAM,CAAA;IACxB,SAAS,EAAE,MAAM,CAAA;CACjB;AAED,MAAM,WAAW,iBAAiB;IACjC,WAAW,EAAE,MAAM,CAAA;IACnB,YAAY,EAAE,MAAM,CAAA;IACpB,gBAAgB,EAAE,MAAM,CAAA;IACxB,SAAS,EAAE,MAAM,CAAA;IACjB,QAAQ,EAAE,MAAM,CAAA;IAChB,SAAS,EAAE,MAAM,CAAA;IACjB,SAAS,EAAE,MAAM,CAAA;IACjB,UAAU,EAAE,MAAM,CAAA;IAClB,UAAU,EAAE,MAAM,CAAA;IAClB,YAAY,EAAE,MAAM,GAAG,IAAI,CAAA;IAC3B,WAAW,EAAE,MAAM,GAAG,IAAI,CAAA;IAC1B,0CAA0C;IAC1C,UAAU,EAAE,MAAM,CAAC,MAAM,EAAE,aAAa,CAAC,CAAA;CACzC;AAmBD;;GAEG;AACH,wBAAgB,kBAAkB,CAAC,YAAY,EAAE,YAAY,GAAG,iBAAiB,CAEhF;AAMD,eAAO,MAAM,kBAAkB,kGA4DtB,CAAA"}

package/dist/plugins/session-stats/plugin.js

@@ -43,7 +43,11 @@ export const sessionStatsPlugin = definePlugin('session-stats')
         switch (event.type) {
             case 'agent_spawned':
                 return withTimestamp({ agentCount: stats.agentCount + 1 });
-            case 'inference_completed': {
+            // inference_completed = main agent turns; auxiliary_inference_completed =
+            // side-channel calls (e.g. context compaction). Both are billed LLM
+            // calls, so both feed the same usage/cost accounting.
+            case 'inference_completed':
+            case 'auxiliary_inference_completed': {
                 const provider = event.metrics.provider;
                 const byProvider = provider
                     ? {

package/dist/plugins/session-stats/plugin.js.map

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package/package.json

@@ -1,6 +1,6 @@
 {
 	"name": "@roj-ai/sdk",
-	"version": "0.1.20",
+	"version": "0.1.21",
 	"type": "module",
 	"main": "./dist/index.js",
 	"exports": {
@@ -135,7 +135,7 @@
 		"type-check": "tsc --noEmit"
 	},
 	"dependencies": {
-		"@roj-ai/transport": "^0.1.20",
+		"@roj-ai/transport": "^0.1.21",
 		"@hono/zod-validator": "0.7.6",
 		"hono": "4.12.5",
 		"ignore": "7.0.5",

package/src/core/agents/agent.ts

@@ -420,7 +420,7 @@ export class Agent {
 			...pendingToolResultMessages,
 		]
 		const messages = [...baseMessages, ...extraMessages]
-		const cachedMessages = applyCacheBreakpoint(messages, extraMessages.length, this.config.cacheTtl)
+		const cachedMessages = applyCacheBreakpoint(messages, extraMessages.length, this.config.cacheTtl, agentState.preamble.length)
 
 		const request: InferenceRequest = {
 			model: this.config.model,
@@ -429,13 +429,28 @@ export class Agent {
 			tools: this.tools.size > 0 ? [...this.tools.values()] : undefined,
 		}
 
-		return this.llmProvider.inference(request, {
+		const result = await this.llmProvider.inference(request, {
 			sessionId: this.store.sessionId,
 			agentId: this.id,
 			signal: this.abortController.signal,
 			fileStore: this.fileStore,
 			providers: this.llmProviders,
 		})
+
+		// Auxiliary calls don't go through emitInferenceCompleted (that event mutates
+		// conversation state), so without this their tokens/cost would be billed but
+		// never show up in session stats or metadata. Emit a stats-only event instead.
+		if (result.ok) {
+			await this.store.emit(withSessionId(
+				this.store.sessionId,
+				llmEvents.create('auxiliary_inference_completed', {
+					agentId: this.id,
+					metrics: result.value.metrics,
+				}),
+			))
+		}
+
+		return result
 	}
 
 	// ============================================================================
@@ -549,6 +564,7 @@ export class Agent {
 			messages,
 			ephemeralParts.length > 0 ? 1 : 0,
 			this.config.cacheTtl,
+			agentState.preamble.length,
 		)
 
 		// 5. LLM inference (with retry)

package/src/core/context/state.ts

@@ -23,6 +23,16 @@ export const contextEvents = createEventsFactory({
 		context_compacted: z4.object({
 			agentId: agentIdSchema,
 			compactedContent: z4.string(),
+			/**
+			 * Display-only snapshot of the messages that were summarized away (the
+			 * "input" of the compaction). Not used for conversation reconstruction —
+			 * that's driven by {@link newConversationHistory}. Optional for backward
+			 * compatibility with events emitted before this field existed.
+			 */
+			originalMessages: z4.array(z4.object({
+				role: z4.enum(['user', 'assistant', 'system']),
+				content: z4.string(),
+			})).optional(),
 			newConversationHistory: z4.array(z4.object({
 				role: z4.enum(['user', 'assistant', 'system']),
 				content: z4.string(),

package/src/core/events/base-event-store.ts

@@ -198,7 +198,9 @@ export abstract class BaseEventStore implements EventStore {
 					metrics.totalEvents += 1
 					break
 
+				// Both normal turns and side-channel calls (e.g. compaction) are billed.
 				case 'inference_completed':
+				case 'auxiliary_inference_completed':
 					if (event.metrics) {
 						metrics.totalTokens += event.metrics.totalTokens ?? 0
 						metrics.inputTokens = (metrics.inputTokens ?? 0) + (event.metrics.promptTokens ?? 0)

package/src/core/events/metadata-utils.ts

@@ -36,7 +36,9 @@ export function computeMetricsFromEvents(events: DomainEvent[]): SessionMetadata
 				metrics.totalAgents++
 				break
 
+			// Both normal turns and side-channel calls (e.g. compaction) are billed.
 			case 'inference_completed':
+			case 'auxiliary_inference_completed':
 				if (event.metrics) {
 					metrics.totalLLMCalls++
 					metrics.totalTokens += event.metrics.totalTokens ?? 0

package/src/core/llm/anthropic.test.ts

@@ -400,6 +400,40 @@ describe('AnthropicProvider buildHttpRequest cache placement', () => {
 		expect(last.content[1].cache_control).toBeUndefined()
 	})
 
+	test('stable prefix + tail: TWO cache_control blocks survive into the HTTP body', async () => {
+		// Mirrors the agent flow: an immutable preamble followed by a churning
+		// conversation tail. applyCacheBreakpoint with cachedPrefixCount marks
+		// BOTH the last preamble message and the tail — both must reach the wire.
+		// Roles alternate so mergeConsecutiveMessages doesn't fold them together.
+		const messages = applyCacheBreakpoint(
+			[
+				{ role: 'user', content: 'preamble part A' },
+				{ role: 'assistant', content: 'preamble part B' }, // last preamble msg → prefix breakpoint
+				{ role: 'user', content: 'conversation turn' },
+				{ role: 'assistant', content: 'tail reply' }, // tail breakpoint
+			],
+			0, // no uncached suffix → tailIdx = 3
+			undefined,
+			2, // cachedPrefixCount → prefixIdx = 1
+		)
+
+		const http = await createProvider().buildHttpRequest(buildRequest(messages))
+		const msgs = getBodyMessages(http.body)
+
+		expect(msgs.length).toBe(4)
+		// Prefix breakpoint on the last preamble message
+		const prefix = msgs[1]
+		expect(prefix.role).toBe('assistant')
+		expect(prefix.content[prefix.content.length - 1].cache_control).toEqual({ type: 'ephemeral' })
+		// Tail breakpoint on the final message
+		const tail = msgs[3]
+		expect(tail.role).toBe('assistant')
+		expect(tail.content[tail.content.length - 1].cache_control).toEqual({ type: 'ephemeral' })
+		// Messages between the two breakpoints stay uncached
+		expect(msgs[0].content[msgs[0].content.length - 1].cache_control).toBeUndefined()
+		expect(msgs[2].content[msgs[2].content.length - 1].cache_control).toBeUndefined()
+	})
+
 	test('no flag on any message: only system prompt has cache_control', async () => {
 		const http = await createProvider().buildHttpRequest(buildRequest([
 			{ role: 'user', content: 'What is 2+2?' },

package/src/core/llm/cache-breakpoints.test.ts

@@ -0,0 +1,55 @@
+import { describe, expect, test } from 'bun:test'
+import type { LLMMessage } from '~/core/agents/state.js'
+import { applyCacheBreakpoint } from './cache-breakpoints.js'
+
+const userMessages = (count: number): LLMMessage[] =>
+	Array.from({ length: count }, (_, i) => ({ role: 'user', content: `m${i}` }))
+
+const cachedIndices = (messages: LLMMessage[]): number[] =>
+	messages.flatMap((m, i) => ('cacheControl' in m && m.cacheControl ? [i] : []))
+
+describe('applyCacheBreakpoint', () => {
+	test('cachedPrefixCount = 0 → single tail breakpoint only (unchanged behaviour)', () => {
+		const messages = userMessages(5)
+		const result = applyCacheBreakpoint(messages, 1)
+		// tail = length - 1 - suffix = 5 - 1 - 1 = 3
+		expect(cachedIndices(result)).toEqual([3])
+	})
+
+	test('cachedPrefixCount > 0 → two breakpoints: prefix end and tail', () => {
+		const messages = userMessages(10)
+		const result = applyCacheBreakpoint(messages, 1, undefined, 3)
+		// prefix = 3 - 1 = 2, tail = 10 - 1 - 1 = 8
+		expect(cachedIndices(result)).toEqual([2, 8])
+	})
+
+	test('prefixIdx === tailIdx → only one breakpoint, no duplicate', () => {
+		// preamble is the whole list, no suffix: tail = 3 - 1 - 0 = 2, prefix = 3 - 1 = 2
+		const messages = userMessages(3)
+		const result = applyCacheBreakpoint(messages, 0, undefined, 3)
+		expect(cachedIndices(result)).toEqual([2])
+	})
+
+	test('cachedPrefixCount larger than messages.length → out-of-range prefix ignored, tail still applied', () => {
+		const messages = userMessages(4)
+		const result = applyCacheBreakpoint(messages, 0, undefined, 99)
+		// prefix = 98 (out of range, ignored), tail = 4 - 1 - 0 = 3
+		expect(cachedIndices(result)).toEqual([3])
+	})
+
+	test('ttl is propagated onto the marked messages', () => {
+		const messages = userMessages(6)
+		const result = applyCacheBreakpoint(messages, 0, '1h', 2)
+		// prefix = 1, tail = 5
+		for (const idx of [1, 5]) {
+			const m = result[idx]
+			expect('cacheControl' in m && m.cacheControl).toEqual({ type: 'ephemeral', ttl: '1h' })
+		}
+	})
+
+	test('does not mutate the input array', () => {
+		const messages = userMessages(5)
+		applyCacheBreakpoint(messages, 0, undefined, 2)
+		expect(cachedIndices(messages)).toEqual([])
+	})
+})

package/src/core/llm/cache-breakpoints.ts

@@ -1,7 +1,7 @@
 import type { LLMMessage, LLMMessageCacheControl } from '~/core/agents/state.js'
 
 /**
- * Mark the prompt cache breakpoint on a message list.
+ * Mark the prompt cache breakpoints on a message list.
  *
  * Flag-based: the target message gets a `cacheControl` marker. Providers that
  * support ephemeral prompt caching (anthropic, openrouter) react to the flag
@@ -10,9 +10,23 @@ import type { LLMMessage, LLMMessageCacheControl } from '~/core/agents/state.js'
  * (text / tool_use / tool_result / image). This matches the API semantics
  * "cache the prefix up to and including this block".
  *
- * Target index is `messages.length - 1 - uncachedSuffixCount`. The suffix is
- * the tail of messages that must remain fresh (e.g. ephemeral session context
- * rebuilt each inference).
+ * Up to two breakpoints are set:
+ *
+ * 1. **Tail breakpoint** at `messages.length - 1 - uncachedSuffixCount`. The
+ *    suffix is the tail of messages that must remain fresh (e.g. ephemeral
+ *    session context rebuilt each inference).
+ *
+ * 2. **Stable prefix breakpoint** at `cachedPrefixCount - 1` (the last preamble
+ *    message), set only when `cachedPrefixCount > 0`. The preamble is byte-
+ *    identical on every call, but the prefix before the tail breakpoint churns
+ *    turn-to-turn for compacting agents (regenerated summary, sliding recent
+ *    window), so the tail breakpoint never produces a stable cache entry for
+ *    the large immutable preamble. Pinning a second breakpoint at the end of
+ *    the preamble lets Anthropic cache that prefix once and read it at 0.1× on
+ *    every inference AND compaction call. Anthropic allows up to 4 breakpoints
+ *    and matches the longest cached prefix, so the two coexist.
+ *
+ * If the prefix and tail indices coincide, only one breakpoint is set.
  *
  * `ttl` opts into Anthropic's 1-hour cache tier (write cost 2× input, read
  * still 0.1×). Useful for long-lived agents where the default 5-minute TTL
@@ -22,26 +36,30 @@ export function applyCacheBreakpoint(
 	messages: LLMMessage[],
 	uncachedSuffixCount: number,
 	ttl?: '5m' | '1h',
+	cachedPrefixCount = 0,
 ): LLMMessage[] {
-	const idx = messages.length - 1 - uncachedSuffixCount
-	if (idx < 0) return messages
-
 	const cacheControl: LLMMessageCacheControl = ttl ? { type: 'ephemeral', ttl } : { type: 'ephemeral' }
-	const target = messages[idx]
 	const result = [...messages]
-	switch (target.role) {
-		case 'user':
-			result[idx] = { ...target, cacheControl }
-			break
-		case 'assistant':
-			result[idx] = { ...target, cacheControl }
-			break
-		case 'system':
-			result[idx] = { ...target, cacheControl }
-			break
-		case 'tool':
-			result[idx] = { ...target, cacheControl }
-			break
+
+	const mark = (idx: number) => {
+		if (idx < 0 || idx >= result.length) return
+		const target = result[idx]
+		switch (target.role) {
+			case 'user':
+			case 'assistant':
+			case 'system':
+			case 'tool':
+				result[idx] = { ...target, cacheControl }
+		}
 	}
+
+	const tailIdx = messages.length - 1 - uncachedSuffixCount
+	// Stable prefix breakpoint at the last preamble message. Pins a cache entry
+	// that survives turn-to-turn churn in the conversation tail (regenerated
+	// summary, sliding recent window), so the immutable preamble is read at 0.1×
+	// on every inference AND compaction call instead of being re-billed each turn.
+	const prefixIdx = cachedPrefixCount - 1
+	if (prefixIdx !== tailIdx) mark(prefixIdx)
+	mark(tailIdx)
 	return result
 }