@h-rig/cli 0.0.6-alpha.63 → 0.0.6-alpha.65

package/dist/src/commands/_policy.js

@@ -5,10 +5,19 @@ import { resolve } from "path";
 
 // packages/cli/src/runner.ts
 import { EventBus } from "@rig/runtime/control-plane/runtime/events";
-import { CliError } from "@rig/runtime/control-plane/errors";
+import { CliError as RuntimeCliError } from "@rig/runtime/control-plane/errors";
 import { evaluate, loadPolicy, resolveAction } from "@rig/runtime/control-plane/runtime/guard";
 import { buildBinary } from "@rig/runtime/control-plane/runtime/isolation";
-import { CliError as CliError2 } from "@rig/runtime/control-plane/errors";
+
+class CliError extends RuntimeCliError {
+  hint;
+  constructor(message, exitCode = 1, options = {}) {
+    super(message, exitCode);
+    if (options.hint?.trim()) {
+      this.hint = options.hint.trim();
+    }
+  }
+}
 function formatCommand(parts) {
   return parts.map((part) => /[^a-zA-Z0-9_./:-]/.test(part) ? JSON.stringify(part) : part).join(" ");
 }
@@ -67,7 +76,7 @@ async function enforceNativeCommandPolicy(context, args, options) {
     appendControlledBashAudit(context, mode, command, args, matchedRuleIds, action === "block" ? "blocked" : action === "warn" ? "warn" : undefined);
   }
   if (action === "block") {
-    throw new CliError2(`Policy blocked command: ${command}`, 126);
+    throw new CliError(`Policy blocked command: ${command}`, 126, { hint: "Review rig/policy/policy.json, or re-run with `--policy-mode observe` to log instead of block." });
   }
 }
 export {

package/dist/src/commands/_preflight.js

@@ -1,10 +1,19 @@
 // @bun
 // packages/cli/src/runner.ts
 import { EventBus } from "@rig/runtime/control-plane/runtime/events";
-import { CliError } from "@rig/runtime/control-plane/errors";
+import { CliError as RuntimeCliError } from "@rig/runtime/control-plane/errors";
 import { evaluate, loadPolicy, resolveAction } from "@rig/runtime/control-plane/runtime/guard";
 import { buildBinary } from "@rig/runtime/control-plane/runtime/isolation";
-import { CliError as CliError2 } from "@rig/runtime/control-plane/errors";
+
+class CliError extends RuntimeCliError {
+  hint;
+  constructor(message, exitCode = 1, options = {}) {
+    super(message, exitCode);
+    if (options.hint?.trim()) {
+      this.hint = options.hint.trim();
+    }
+  }
+}
 
 // packages/cli/src/commands/_preflight.ts
 import { ensureProjectMainFreshBeforeRun } from "@rig/runtime/control-plane/project-main-pre-run-sync";
@@ -31,7 +40,7 @@ function readJsonFile(path) {
   try {
     return JSON.parse(readFileSync(path, "utf8"));
   } catch (error) {
-    throw new CliError2(`Invalid Rig connection state at ${path}: ${error instanceof Error ? error.message : String(error)}`, 1);
+    throw new CliError(`Invalid Rig connection state at ${path}: ${error instanceof Error ? error.message : String(error)}`, 1, { hint: "Fix or delete that file, then re-select a server with `rig server use <alias|local>`." });
   }
 }
 function writeJsonFile(path, value) {
@@ -95,7 +104,7 @@ function resolveSelectedConnection(projectRoot, options = {}) {
   const global = readGlobalConnections(options);
   const connection = global.connections[repo.selected];
   if (!connection) {
-    throw new CliError2(`Selected Rig server "${repo.selected}" was not found. Run \`rig server list\` or \`rig server use local\`.`, 1);
+    throw new CliError(`Selected Rig server "${repo.selected}" was not found. Run \`rig server list\` or \`rig server use local\`.`, 1);
   }
   return { alias: repo.selected, connection, serverProjectRoot: repo.serverProjectRoot };
 }
@@ -171,7 +180,7 @@ async function ensureServerForCli(projectRoot) {
     };
   } catch (error) {
     if (error instanceof Error) {
-      throw new CliError2(error.message, 1);
+      throw new CliError(error.message, 1);
     }
     throw error;
   }
@@ -221,15 +230,64 @@ function diagnosticMessage(payload) {
   });
   return messages.length > 0 ? messages.join("; ") : null;
 }
+var serverReachabilityCache = new Map;
+async function probeServerReachability(baseUrl, authToken) {
+  try {
+    const response = await fetch(`${baseUrl.replace(/\/+$/, "")}/api/server/status`, {
+      headers: mergeHeaders(undefined, authToken),
+      signal: AbortSignal.timeout(1500)
+    });
+    return response.ok;
+  } catch {
+    return false;
+  }
+}
+function cachedServerReachability(projectRoot, baseUrl, authToken) {
+  const key = resolve2(projectRoot);
+  const cached = serverReachabilityCache.get(key);
+  if (cached)
+    return cached;
+  const probe = probeServerReachability(baseUrl, authToken);
+  serverReachabilityCache.set(key, probe);
+  return probe;
+}
+function describeSelectedServer(projectRoot, server) {
+  try {
+    const selected = resolveSelectedConnection(projectRoot);
+    if (selected) {
+      return {
+        alias: selected.alias,
+        target: selected.connection.kind === "remote" ? selected.connection.baseUrl : server.baseUrl
+      };
+    }
+  } catch {}
+  return { alias: server.connectionKind === "remote" ? "remote" : "local", target: server.baseUrl };
+}
+async function buildServerFailureContext(projectRoot, server) {
+  const { alias, target } = describeSelectedServer(projectRoot, server);
+  const reachable = await cachedServerReachability(projectRoot, server.baseUrl, server.authToken);
+  const reachability = reachable ? "server is reachable" : "server is unreachable";
+  return {
+    contextLine: `Currently connected to: ${alias} at ${target} (${reachability}).`,
+    hint: "Check the selected server with `rig server status`, or switch with `rig server use <alias|local>`."
+  };
+}
 async function requestServerJson(context, pathname, init = {}) {
   const server = await ensureServerForCli(context.projectRoot);
   const headers = mergeHeaders(init.headers, server.authToken);
   if (server.serverProjectRoot)
     headers.set("x-rig-project-root", server.serverProjectRoot);
-  const response = await fetch(`${server.baseUrl}${pathname}`, {
-    ...init,
-    headers
-  });
+  let response;
+  try {
+    response = await fetch(`${server.baseUrl}${pathname}`, {
+      ...init,
+      headers
+    });
+  } catch (error) {
+    const failure = await buildServerFailureContext(context.projectRoot, server);
+    throw new CliError(`Rig server request failed: ${error instanceof Error ? error.message : String(error)}
+${failure.contextLine}`, 1, { hint: failure.hint });
+  }
   const text = await response.text();
   const payload = text.trim().length > 0 ? (() => {
     try {
@@ -241,7 +299,9 @@ async function requestServerJson(context, pathname, init = {}) {
   if (!response.ok) {
     const diagnostics = diagnosticMessage(payload);
     const detail = diagnostics ?? (text || response.statusText);
-    throw new CliError2(`Rig server request failed (${response.status}): ${detail}`, 1);
+    const failure = await buildServerFailureContext(context.projectRoot, server);
+    throw new CliError(`Rig server request failed (${response.status}): ${detail}
+${failure.contextLine}`, 1, { hint: failure.hint });
   }
   return payload;
 }
@@ -411,9 +471,9 @@ async function runFastTaskRunPreflight(context, options = {}) {
   if (failures.length > 0) {
     const summary = failures.map((check) => `${check.label}${check.detail ? `: ${check.detail}` : ""}`).join("; ");
     if (failures.some((check) => check.id === "duplicate-active-run") && taskId) {
-      throw new CliError2(`Task ${taskId} already has an active Rig run. ${summary}`, 1);
+      throw new CliError(`Task ${taskId} already has an active Rig run. ${summary}`, 1, { hint: `Attach to it with \`rig run attach <run-id> --follow\`, or stop it first with \`rig run stop <run-id>\`.` });
     }
-    throw new CliError2(`Task run preflight failed: ${summary}`, 1);
+    throw new CliError(`Task run preflight failed: ${summary}`, 1, { hint: "Run `rig doctor` to diagnose, then retry `rig task run`." });
   }
   return { ok: true, checks };
 }
@@ -430,7 +490,7 @@ async function runProjectMainSyncPreflight(context, options) {
     runBootstrap: async () => {
       const bootstrap = await context.runCommand(["bun", "run", "bootstrap"]);
       if (bootstrap.exitCode !== 0) {
-        throw new CliError2(bootstrap.stderr || bootstrap.stdout || "bun run bootstrap failed during project pre-run sync", bootstrap.exitCode || 1);
+        throw new CliError(bootstrap.stderr || bootstrap.stdout || "bun run bootstrap failed during project pre-run sync", bootstrap.exitCode || 1);
       }
     }
   });

package/dist/src/commands/_run-driver-helpers.js

@@ -5,19 +5,29 @@ import { resolve as resolve3 } from "path";
 
 // packages/cli/src/runner.ts
 import { EventBus } from "@rig/runtime/control-plane/runtime/events";
-import { CliError } from "@rig/runtime/control-plane/errors";
+import { CliError as RuntimeCliError } from "@rig/runtime/control-plane/errors";
 import { evaluate, loadPolicy, resolveAction } from "@rig/runtime/control-plane/runtime/guard";
 import { buildBinary } from "@rig/runtime/control-plane/runtime/isolation";
-import { CliError as CliError2 } from "@rig/runtime/control-plane/errors";
+
+class CliError extends RuntimeCliError {
+  hint;
+  constructor(message, exitCode = 1, options = {}) {
+    super(message, exitCode);
+    if (options.hint?.trim()) {
+      this.hint = options.hint.trim();
+    }
+  }
+}
 
 // packages/cli/src/commands/_run-driver-helpers.ts
 import {
-  appendRunLifecycleEvent,
+  appendRunJournalEvent,
   appendRunLogEntry,
   appendRunTimelineEntry,
   patchAuthorityRunRecord,
   readAuthorityRun as readAuthorityRun2,
   resolveAuthorityRunDir,
+  setAuthorityRunStatus,
   writeJsonFile
 } from "@rig/runtime/control-plane/authority-files";
 import { taskLookup } from "@rig/runtime/control-plane/native/task-ops";
@@ -67,7 +77,17 @@ function readLatestBeadRecord(projectRoot, taskId) {
 function patchAuthorityRun(projectRoot, runId, patch) {
   const next = patchAuthorityRunRecord(projectRoot, runId, patch);
   if (!next) {
-    throw new CliError2(`Run not found: ${runId}`, 2);
+    throw new CliError(`Run not found: ${runId}`, 2, { hint: "Run `rig run list` to see recorded runs." });
+  }
+  return next;
+}
+function setRunStatusOrFail(projectRoot, runId, to, options = {}) {
+  const next = setAuthorityRunStatus(projectRoot, runId, to, {
+    ...options,
+    actor: { kind: "agent" }
+  });
+  if (!next) {
+    throw new CliError(`Run not found: ${runId}`, 2, { hint: "Run `rig run list` to see recorded runs." });
   }
   return next;
 }
@@ -172,7 +192,12 @@ function emitServerRunEvent(event) {
   console.log(`__RIG_RUN_EVENT__${JSON.stringify({ ...event, at: new Date().toISOString() })}`);
   if (runEventSinkProjectRoot) {
     try {
-      appendRunLifecycleEvent(runEventSinkProjectRoot, event.runId, { ...event });
+      if (event.type === "status" || event.type === "completed" || event.type === "failed") {
+        appendRunJournalEvent(runEventSinkProjectRoot, event.runId, {
+          type: "timeline-entry",
+          payload: { kind: "driver-event", ...event }
+        });
+      }
     } catch {}
     ringServerRunDoorbell(event.runId);
   }
@@ -306,6 +331,7 @@ function renderSourceScopeValidation(task, validation) {
 export {
   touchAuthorityRun,
   startRunAction,
+  setRunStatusOrFail,
   patchAuthorityRun,
   emitServerRunEvent,
   configureRunEventSink,

package/dist/src/commands/_run-replay.js

@@ -5,7 +5,7 @@ import { join, resolve } from "path";
 import {
   readAuthorityRun,
   readJsonlFile,
-  runLifecycleLogPath
+  runJournalPath
 } from "@rig/runtime/control-plane/authority-files";
 function asRecord(value) {
   return value && typeof value === "object" && !Array.isArray(value) ? value : null;
@@ -103,7 +103,7 @@ function resolveRunSessionFile(record) {
   }
 }
 function buildRunReplay(projectRoot, runId, options = {}) {
-  const logPath = runLifecycleLogPath(projectRoot, runId);
+  const logPath = runJournalPath(projectRoot, runId);
   const record = readAuthorityRun(projectRoot, runId);
   const lifecycleEntries = readJsonlFile(logPath).map((entry) => asRecord(entry)).filter((entry) => entry !== null);
   const merged = lifecycleEntries.map((entry) => ({

package/dist/src/commands/_server-client.js

@@ -5,10 +5,19 @@ import { resolve as resolve2 } from "path";
 
 // packages/cli/src/runner.ts
 import { EventBus } from "@rig/runtime/control-plane/runtime/events";
-import { CliError } from "@rig/runtime/control-plane/errors";
+import { CliError as RuntimeCliError } from "@rig/runtime/control-plane/errors";
 import { evaluate, loadPolicy, resolveAction } from "@rig/runtime/control-plane/runtime/guard";
 import { buildBinary } from "@rig/runtime/control-plane/runtime/isolation";
-import { CliError as CliError2 } from "@rig/runtime/control-plane/errors";
+
+class CliError extends RuntimeCliError {
+  hint;
+  constructor(message, exitCode = 1, options = {}) {
+    super(message, exitCode);
+    if (options.hint?.trim()) {
+      this.hint = options.hint.trim();
+    }
+  }
+}
 
 // packages/cli/src/commands/_server-client.ts
 import { ensureLocalRigServerConnection } from "@rig/runtime/local-server";
@@ -35,7 +44,7 @@ function readJsonFile(path) {
   try {
     return JSON.parse(readFileSync(path, "utf8"));
   } catch (error) {
-    throw new CliError2(`Invalid Rig connection state at ${path}: ${error instanceof Error ? error.message : String(error)}`, 1);
+    throw new CliError(`Invalid Rig connection state at ${path}: ${error instanceof Error ? error.message : String(error)}`, 1, { hint: "Fix or delete that file, then re-select a server with `rig server use <alias|local>`." });
   }
 }
 function writeJsonFile(path, value) {
@@ -99,7 +108,7 @@ function resolveSelectedConnection(projectRoot, options = {}) {
   const global = readGlobalConnections(options);
   const connection = global.connections[repo.selected];
   if (!connection) {
-    throw new CliError2(`Selected Rig server "${repo.selected}" was not found. Run \`rig server list\` or \`rig server use local\`.`, 1);
+    throw new CliError(`Selected Rig server "${repo.selected}" was not found. Run \`rig server list\` or \`rig server use local\`.`, 1);
   }
   return { alias: repo.selected, connection, serverProjectRoot: repo.serverProjectRoot };
 }
@@ -176,7 +185,7 @@ async function ensureServerForCli(projectRoot) {
     };
   } catch (error) {
     if (error instanceof Error) {
-      throw new CliError2(error.message, 1);
+      throw new CliError(error.message, 1);
     }
     throw error;
   }
@@ -236,15 +245,64 @@ function diagnosticMessage(payload) {
   });
   return messages.length > 0 ? messages.join("; ") : null;
 }
+var serverReachabilityCache = new Map;
+async function probeServerReachability(baseUrl, authToken) {
+  try {
+    const response = await fetch(`${baseUrl.replace(/\/+$/, "")}/api/server/status`, {
+      headers: mergeHeaders(undefined, authToken),
+      signal: AbortSignal.timeout(1500)
+    });
+    return response.ok;
+  } catch {
+    return false;
+  }
+}
+function cachedServerReachability(projectRoot, baseUrl, authToken) {
+  const key = resolve2(projectRoot);
+  const cached = serverReachabilityCache.get(key);
+  if (cached)
+    return cached;
+  const probe = probeServerReachability(baseUrl, authToken);
+  serverReachabilityCache.set(key, probe);
+  return probe;
+}
+function describeSelectedServer(projectRoot, server) {
+  try {
+    const selected = resolveSelectedConnection(projectRoot);
+    if (selected) {
+      return {
+        alias: selected.alias,
+        target: selected.connection.kind === "remote" ? selected.connection.baseUrl : server.baseUrl
+      };
+    }
+  } catch {}
+  return { alias: server.connectionKind === "remote" ? "remote" : "local", target: server.baseUrl };
+}
+async function buildServerFailureContext(projectRoot, server) {
+  const { alias, target } = describeSelectedServer(projectRoot, server);
+  const reachable = await cachedServerReachability(projectRoot, server.baseUrl, server.authToken);
+  const reachability = reachable ? "server is reachable" : "server is unreachable";
+  return {
+    contextLine: `Currently connected to: ${alias} at ${target} (${reachability}).`,
+    hint: "Check the selected server with `rig server status`, or switch with `rig server use <alias|local>`."
+  };
+}
 async function requestServerJson(context, pathname, init = {}) {
   const server = await ensureServerForCli(context.projectRoot);
   const headers = mergeHeaders(init.headers, server.authToken);
   if (server.serverProjectRoot)
     headers.set("x-rig-project-root", server.serverProjectRoot);
-  const response = await fetch(`${server.baseUrl}${pathname}`, {
-    ...init,
-    headers
-  });
+  let response;
+  try {
+    response = await fetch(`${server.baseUrl}${pathname}`, {
+      ...init,
+      headers
+    });
+  } catch (error) {
+    const failure = await buildServerFailureContext(context.projectRoot, server);
+    throw new CliError(`Rig server request failed: ${error instanceof Error ? error.message : String(error)}
+${failure.contextLine}`, 1, { hint: failure.hint });
+  }
   const text = await response.text();
   const payload = text.trim().length > 0 ? (() => {
     try {
@@ -256,7 +314,9 @@ async function requestServerJson(context, pathname, init = {}) {
   if (!response.ok) {
     const diagnostics = diagnosticMessage(payload);
     const detail = diagnostics ?? (text || response.statusText);
-    throw new CliError2(`Rig server request failed (${response.status}): ${detail}`, 1);
+    const failure = await buildServerFailureContext(context.projectRoot, server);
+    throw new CliError(`Rig server request failed (${response.status}): ${detail}
+${failure.contextLine}`, 1, { hint: failure.hint });
   }
   return payload;
 }
@@ -265,7 +325,7 @@ async function listWorkspaceTasksViaServer(context, filters = {}) {
   appendTaskFilterParams(url, filters);
   const payload = await requestServerJson(context, `${url.pathname}${url.search}`);
   if (!Array.isArray(payload)) {
-    throw new CliError2("Rig server returned an invalid task list payload.", 1);
+    throw new CliError("Rig server returned an invalid task list payload.", 1, { hint: "Check the selected server with `rig server status`; mixed CLI/server versions can mismatch \u2014 try `rig doctor`." });
   }
   return payload.flatMap((entry) => entry && typeof entry === "object" && !Array.isArray(entry) ? [entry] : []);
 }
@@ -281,7 +341,7 @@ async function selectNextWorkspaceTaskViaServer(context, filters = {}) {
   appendTaskFilterParams(url, filters);
   const payload = await requestServerJson(context, `${url.pathname}${url.search}`);
   if (!payload || typeof payload !== "object" || Array.isArray(payload)) {
-    throw new CliError2("Rig server returned an invalid next-task payload.", 1);
+    throw new CliError("Rig server returned an invalid next-task payload.", 1, { hint: "Check the selected server with `rig server status`; try `rig task list` to see the raw task set." });
   }
   const record = payload;
   const rawTask = record.task;
@@ -348,14 +408,14 @@ async function switchServerProjectRootViaServer(context, projectRoot, options =
     }
   }
   if (!switched) {
-    throw new CliError2(`Rig server did not accept project-root switch to ${projectRoot} before timeout (${lastError instanceof Error ? lastError.message : String(lastError ?? "no response")}).`, 1);
+    throw new CliError(`Rig server did not accept project-root switch to ${projectRoot} before timeout (${lastError instanceof Error ? lastError.message : String(lastError ?? "no response")}).`, 1);
   }
   const record = switched && typeof switched === "object" && !Array.isArray(switched) ? switched : {};
   if (record.ok === true) {
     writeRepoServerProjectRoot(context.projectRoot, projectRoot);
     return { ok: true, switched: record };
   }
-  throw new CliError2(`Rig server rejected project-root scope ${projectRoot}: ${String(record.message ?? record.error ?? "unknown error")}`, 1);
+  throw new CliError(`Rig server rejected project-root scope ${projectRoot}: ${String(record.message ?? record.error ?? "unknown error")}`, 1);
 }
 async function listRunsViaServer(context, options = {}) {
   const url = new URL("http://rig.local/api/runs");
@@ -514,11 +574,11 @@ async function submitTaskRunViaServer(context, input) {
     })
   });
   if (!payload || typeof payload !== "object" || Array.isArray(payload)) {
-    throw new CliError2("Rig server returned an invalid run submission payload.", 1);
+    throw new CliError("Rig server returned an invalid run submission payload.", 1, { hint: "Check `rig server status` and retry; `rig run list` shows whether the run was created anyway." });
   }
   const runId = payload.runId;
   if (typeof runId !== "string" || runId.trim().length === 0) {
-    throw new CliError2("Rig server returned no runId for the submitted run.", 1);
+    throw new CliError("Rig server returned no runId for the submitted run.", 1, { hint: "Check `rig run list` \u2014 the run may still have been created; otherwise retry the submission." });
   }
   return { runId };
 }

package/dist/src/commands/_snapshot-upload.js

@@ -9,10 +9,19 @@ import { resolve as resolve2 } from "path";
 
 // packages/cli/src/runner.ts
 import { EventBus } from "@rig/runtime/control-plane/runtime/events";
-import { CliError } from "@rig/runtime/control-plane/errors";
+import { CliError as RuntimeCliError } from "@rig/runtime/control-plane/errors";
 import { evaluate, loadPolicy, resolveAction } from "@rig/runtime/control-plane/runtime/guard";
 import { buildBinary } from "@rig/runtime/control-plane/runtime/isolation";
-import { CliError as CliError2 } from "@rig/runtime/control-plane/errors";
+
+class CliError extends RuntimeCliError {
+  hint;
+  constructor(message, exitCode = 1, options = {}) {
+    super(message, exitCode);
+    if (options.hint?.trim()) {
+      this.hint = options.hint.trim();
+    }
+  }
+}
 
 // packages/cli/src/commands/_server-client.ts
 import { ensureLocalRigServerConnection } from "@rig/runtime/local-server";
@@ -39,7 +48,7 @@ function readJsonFile(path) {
   try {
     return JSON.parse(readFileSync(path, "utf8"));
   } catch (error) {
-    throw new CliError2(`Invalid Rig connection state at ${path}: ${error instanceof Error ? error.message : String(error)}`, 1);
+    throw new CliError(`Invalid Rig connection state at ${path}: ${error instanceof Error ? error.message : String(error)}`, 1, { hint: "Fix or delete that file, then re-select a server with `rig server use <alias|local>`." });
   }
 }
 function writeJsonFile(path, value) {
@@ -103,7 +112,7 @@ function resolveSelectedConnection(projectRoot, options = {}) {
   const global = readGlobalConnections(options);
   const connection = global.connections[repo.selected];
   if (!connection) {
-    throw new CliError2(`Selected Rig server "${repo.selected}" was not found. Run \`rig server list\` or \`rig server use local\`.`, 1);
+    throw new CliError(`Selected Rig server "${repo.selected}" was not found. Run \`rig server list\` or \`rig server use local\`.`, 1);
   }
   return { alias: repo.selected, connection, serverProjectRoot: repo.serverProjectRoot };
 }
@@ -176,7 +185,7 @@ async function ensureServerForCli(projectRoot) {
     };
   } catch (error) {
     if (error instanceof Error) {
-      throw new CliError2(error.message, 1);
+      throw new CliError(error.message, 1);
     }
     throw error;
   }
@@ -226,15 +235,64 @@ function diagnosticMessage(payload) {
   });
   return messages.length > 0 ? messages.join("; ") : null;
 }
+var serverReachabilityCache = new Map;
+async function probeServerReachability(baseUrl, authToken) {
+  try {
+    const response = await fetch(`${baseUrl.replace(/\/+$/, "")}/api/server/status`, {
+      headers: mergeHeaders(undefined, authToken),
+      signal: AbortSignal.timeout(1500)
+    });
+    return response.ok;
+  } catch {
+    return false;
+  }
+}
+function cachedServerReachability(projectRoot, baseUrl, authToken) {
+  const key = resolve2(projectRoot);
+  const cached = serverReachabilityCache.get(key);
+  if (cached)
+    return cached;
+  const probe = probeServerReachability(baseUrl, authToken);
+  serverReachabilityCache.set(key, probe);
+  return probe;
+}
+function describeSelectedServer(projectRoot, server) {
+  try {
+    const selected = resolveSelectedConnection(projectRoot);
+    if (selected) {
+      return {
+        alias: selected.alias,
+        target: selected.connection.kind === "remote" ? selected.connection.baseUrl : server.baseUrl
+      };
+    }
+  } catch {}
+  return { alias: server.connectionKind === "remote" ? "remote" : "local", target: server.baseUrl };
+}
+async function buildServerFailureContext(projectRoot, server) {
+  const { alias, target } = describeSelectedServer(projectRoot, server);
+  const reachable = await cachedServerReachability(projectRoot, server.baseUrl, server.authToken);
+  const reachability = reachable ? "server is reachable" : "server is unreachable";
+  return {
+    contextLine: `Currently connected to: ${alias} at ${target} (${reachability}).`,
+    hint: "Check the selected server with `rig server status`, or switch with `rig server use <alias|local>`."
+  };
+}
 async function requestServerJson(context, pathname, init = {}) {
   const server = await ensureServerForCli(context.projectRoot);
   const headers = mergeHeaders(init.headers, server.authToken);
   if (server.serverProjectRoot)
     headers.set("x-rig-project-root", server.serverProjectRoot);
-  const response = await fetch(`${server.baseUrl}${pathname}`, {
-    ...init,
-    headers
-  });
+  let response;
+  try {
+    response = await fetch(`${server.baseUrl}${pathname}`, {
+      ...init,
+      headers
+    });
+  } catch (error) {
+    const failure = await buildServerFailureContext(context.projectRoot, server);
+    throw new CliError(`Rig server request failed: ${error instanceof Error ? error.message : String(error)}
+${failure.contextLine}`, 1, { hint: failure.hint });
+  }
   const text = await response.text();
   const payload = text.trim().length > 0 ? (() => {
     try {
@@ -246,7 +304,9 @@ async function requestServerJson(context, pathname, init = {}) {
   if (!response.ok) {
     const diagnostics = diagnosticMessage(payload);
     const detail = diagnostics ?? (text || response.statusText);
-    throw new CliError2(`Rig server request failed (${response.status}): ${detail}`, 1);
+    const failure = await buildServerFailureContext(context.projectRoot, server);
+    throw new CliError(`Rig server request failed (${response.status}): ${detail}
+${failure.contextLine}`, 1, { hint: failure.hint });
   }
   return payload;
 }