fix: skip cooldowned providers during model failover (#2143) (thanks @YiWang24)

When all auth profiles for a provider are in cooldown, the failover
mechanism now skips that provider immediately rather than attempting
and waiting for the cooldown error. This prevents long delays when
multiple OAuth providers fail in sequence.

CHANGELOG.md

@@ -6,6 +6,7 @@ Docs: https://docs.clawd.bot
 Status: unreleased.
 
 ### Changes
+- Agents: summarize dropped messages during compaction safeguard pruning. (#2509) Thanks @jogi47.
 - Skills: add multi-image input support to Nano Banana Pro skill. (#1958) Thanks @tyler6204.
 - Agents: honor tools.exec.safeBins in exec allowlist checks. (#2281)
 - Matrix: switch plugin SDK to @vector-im/matrix-bot-sdk.
@@ -65,9 +66,10 @@ Status: unreleased.
 - CLI: avoid loading config for global help/version while registering plugin commands. (#2212) Thanks @dial481.
 - Agents: include memory.md when bootstrapping memory context. (#2318) Thanks @czekaj.
 - Agents: release session locks on process termination and cover more signals. (#2483) Thanks @janeexai.
+- Agents: skip cooldowned providers during model failover. (#2143) Thanks @YiWang24.
 - Telegram: harden polling + retry behavior for transient network errors and Node 22 transport issues. (#2420) Thanks @techboss.
 - Telegram: wrap reasoning italics per line to avoid raw underscores. (#2181) Thanks @YuriNachos.
-- Telegram: log fetch/API errors in delivery to avoid unhandled rejections. (#2492) Thanks @altryne.
+- Telegram: centralize API error logging for delivery and bot calls. (#2492) Thanks @altryne.
 - Voice Call: enforce Twilio webhook signature verification for ngrok URLs; disable ngrok free tier bypass by default.
 - Security: harden Tailscale Serve auth by validating identity via local tailscaled before trusting headers.
 - Build: align memory-core peer dependency with lockfile.

README.md

@@ -484,29 +484,29 @@ Thanks to all clawtributors:
   <a href="https://github.com/lc0rp"><img src="https://avatars.githubusercontent.com/u/2609441?v=4&s=48" width="48" height="48" alt="lc0rp" title="lc0rp"/></a> <a href="https://github.com/mousberg"><img src="https://avatars.githubusercontent.com/u/57605064?v=4&s=48" width="48" height="48" alt="mousberg" title="mousberg"/></a> <a href="https://github.com/mteam88"><img src="https://avatars.githubusercontent.com/u/84196639?v=4&s=48" width="48" height="48" alt="mteam88" title="mteam88"/></a> <a href="https://github.com/hirefrank"><img src="https://avatars.githubusercontent.com/u/183158?v=4&s=48" width="48" height="48" alt="hirefrank" title="hirefrank"/></a> <a href="https://github.com/joeynyc"><img src="https://avatars.githubusercontent.com/u/17919866?v=4&s=48" width="48" height="48" alt="joeynyc" title="joeynyc"/></a> <a href="https://github.com/orlyjamie"><img src="https://avatars.githubusercontent.com/u/6668807?v=4&s=48" width="48" height="48" alt="orlyjamie" title="orlyjamie"/></a> <a href="https://github.com/dbhurley"><img src="https://avatars.githubusercontent.com/u/5251425?v=4&s=48" width="48" height="48" alt="dbhurley" title="dbhurley"/></a> <a href="https://github.com/mbelinky"><img src="https://avatars.githubusercontent.com/u/132747814?v=4&s=48" width="48" height="48" alt="Mariano Belinky" title="Mariano Belinky"/></a> <a href="https://github.com/omniwired"><img src="https://avatars.githubusercontent.com/u/322761?v=4&s=48" width="48" height="48" alt="Eng. Juan Combetto" title="Eng. Juan Combetto"/></a> <a href="https://github.com/TSavo"><img src="https://avatars.githubusercontent.com/u/877990?v=4&s=48" width="48" height="48" alt="TSavo" title="TSavo"/></a>
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+  <a href="https://github.com/Seredeep"><img src="https://avatars.githubusercontent.com/u/22802816?v=4&s=48" width="48" height="48" alt="Seredeep" title="Seredeep"/></a> <a href="https://github.com/sergical"><img src="https://avatars.githubusercontent.com/u/3760543?v=4&s=48" width="48" height="48" alt="sergical" title="sergical"/></a> <a href="https://github.com/shiv19"><img src="https://avatars.githubusercontent.com/u/9407019?v=4&s=48" width="48" height="48" alt="shiv19" title="shiv19"/></a> <a href="https://github.com/shiyuanhai"><img src="https://avatars.githubusercontent.com/u/1187370?v=4&s=48" width="48" height="48" alt="shiyuanhai" title="shiyuanhai"/></a> <a href="https://github.com/siraht"><img src="https://avatars.githubusercontent.com/u/73152895?v=4&s=48" width="48" height="48" alt="siraht" title="siraht"/></a> <a href="https://github.com/snopoke"><img src="https://avatars.githubusercontent.com/u/249606?v=4&s=48" width="48" height="48" alt="snopoke" title="snopoke"/></a> <a href="https://github.com/Suksham-sharma"><img src="https://avatars.githubusercontent.com/u/94667656?v=4&s=48" width="48" height="48" alt="Suksham-sharma" title="Suksham-sharma"/></a> <a href="https://github.com/search?q=techboss"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="techboss" title="techboss"/></a> <a href="https://github.com/testingabc321"><img src="https://avatars.githubusercontent.com/u/8577388?v=4&s=48" width="48" height="48" alt="testingabc321" title="testingabc321"/></a> <a href="https://github.com/search?q=The%20Admiral"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="The Admiral" title="The Admiral"/></a>
+  <a href="https://github.com/thesash"><img src="https://avatars.githubusercontent.com/u/1166151?v=4&s=48" width="48" height="48" alt="thesash" title="thesash"/></a> <a href="https://github.com/search?q=Ubuntu"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Ubuntu" title="Ubuntu"/></a> <a href="https://github.com/voidserf"><img src="https://avatars.githubusercontent.com/u/477673?v=4&s=48" width="48" height="48" alt="voidserf" title="voidserf"/></a> <a href="https://github.com/search?q=Vultr-Clawd%20Admin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Vultr-Clawd Admin" title="Vultr-Clawd Admin"/></a> <a href="https://github.com/search?q=Wimmie"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Wimmie" title="Wimmie"/></a> <a href="https://github.com/search?q=wolfred"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="wolfred" title="wolfred"/></a> <a href="https://github.com/wstock"><img src="https://avatars.githubusercontent.com/u/1394687?v=4&s=48" width="48" height="48" alt="wstock" title="wstock"/></a> <a href="https://github.com/yazinsai"><img src="https://avatars.githubusercontent.com/u/1846034?v=4&s=48" width="48" height="48" alt="yazinsai" title="yazinsai"/></a> <a href="https://github.com/search?q=ymat19"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="ymat19" title="ymat19"/></a> <a href="https://github.com/search?q=Zach%20Knickerbocker"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Zach Knickerbocker" title="Zach Knickerbocker"/></a>
+  <a href="https://github.com/0xJonHoldsCrypto"><img src="https://avatars.githubusercontent.com/u/81202085?v=4&s=48" width="48" height="48" alt="0xJonHoldsCrypto" title="0xJonHoldsCrypto"/></a> <a href="https://github.com/aaronn"><img src="https://avatars.githubusercontent.com/u/1653630?v=4&s=48" width="48" height="48" alt="aaronn" title="aaronn"/></a> <a href="https://github.com/Alphonse-arianee"><img src="https://avatars.githubusercontent.com/u/254457365?v=4&s=48" width="48" height="48" alt="Alphonse-arianee" title="Alphonse-arianee"/></a> <a href="https://github.com/atalovesyou"><img src="https://avatars.githubusercontent.com/u/3534502?v=4&s=48" width="48" height="48" alt="atalovesyou" title="atalovesyou"/></a> <a href="https://github.com/search?q=Azade"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Azade" title="Azade"/></a> <a href="https://github.com/carlulsoe"><img src="https://avatars.githubusercontent.com/u/34673973?v=4&s=48" width="48" height="48" alt="carlulsoe" title="carlulsoe"/></a> <a href="https://github.com/search?q=ddyo"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="ddyo" title="ddyo"/></a> <a href="https://github.com/search?q=Erik"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Erik" title="Erik"/></a> <a href="https://github.com/hougangdev"><img src="https://avatars.githubusercontent.com/u/105773686?v=4&s=48" width="48" height="48" alt="hougangdev" title="hougangdev"/></a> <a href="https://github.com/latitudeki5223"><img src="https://avatars.githubusercontent.com/u/119656367?v=4&s=48" width="48" height="48" alt="latitudeki5223" title="latitudeki5223"/></a>
+  <a href="https://github.com/search?q=Manuel%20Maly"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Manuel Maly" title="Manuel Maly"/></a> <a href="https://github.com/search?q=Mourad%20Boustani"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Mourad Boustani" title="Mourad Boustani"/></a> <a href="https://github.com/odrobnik"><img src="https://avatars.githubusercontent.com/u/333270?v=4&s=48" width="48" height="48" alt="odrobnik" title="odrobnik"/></a> <a href="https://github.com/pcty-nextgen-ios-builder"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="pcty-nextgen-ios-builder" title="pcty-nextgen-ios-builder"/></a> <a href="https://github.com/search?q=Quentin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Quentin" title="Quentin"/></a> <a href="https://github.com/search?q=Randy%20Torres"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Randy Torres" title="Randy Torres"/></a> <a href="https://github.com/rhjoh"><img src="https://avatars.githubusercontent.com/u/105699450?v=4&s=48" width="48" height="48" alt="rhjoh" title="rhjoh"/></a> <a href="https://github.com/ronak-guliani"><img src="https://avatars.githubusercontent.com/u/23518228?v=4&s=48" width="48" height="48" alt="ronak-guliani" title="ronak-guliani"/></a> <a href="https://github.com/search?q=William%20Stock"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="William Stock" title="William Stock"/></a>
 </p>

src/agents/auth-profiles/oauth.fallback-to-main-agent.test.ts

@@ -1,30 +1,44 @@
-import fs from "node:fs";
+import fs from "node:fs/promises";
 import path from "node:path";
 import os from "node:os";
 import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import { resolveApiKeyForProfile } from "./oauth.js";
+import { ensureAuthProfileStore } from "./store.js";
 import type { AuthProfileStore } from "./types.js";
 
-describe("resolveApiKeyForProfile", () => {
+describe("resolveApiKeyForProfile fallback to main agent", () => {
+  const previousStateDir = process.env.CLAWDBOT_STATE_DIR;
+  const previousAgentDir = process.env.CLAWDBOT_AGENT_DIR;
+  const previousPiAgentDir = process.env.PI_CODING_AGENT_DIR;
   let tmpDir: string;
   let mainAgentDir: string;
   let secondaryAgentDir: string;
 
   beforeEach(async () => {
-    tmpDir = await fs.promises.mkdtemp(path.join(os.tmpdir(), "oauth-test-"));
+    tmpDir = await fs.mkdtemp(path.join(os.tmpdir(), "oauth-fallback-test-"));
     mainAgentDir = path.join(tmpDir, "agents", "main", "agent");
     secondaryAgentDir = path.join(tmpDir, "agents", "kids", "agent");
-    await fs.promises.mkdir(mainAgentDir, { recursive: true });
-    await fs.promises.mkdir(secondaryAgentDir, { recursive: true });
+    await fs.mkdir(mainAgentDir, { recursive: true });
+    await fs.mkdir(secondaryAgentDir, { recursive: true });
 
-    // Set env to use our temp dir
+    // Set environment variables so resolveClawdbotAgentDir() returns mainAgentDir
     process.env.CLAWDBOT_STATE_DIR = tmpDir;
+    process.env.CLAWDBOT_AGENT_DIR = mainAgentDir;
+    process.env.PI_CODING_AGENT_DIR = mainAgentDir;
   });
 
   afterEach(async () => {
-    delete process.env.CLAWDBOT_STATE_DIR;
-    await fs.promises.rm(tmpDir, { recursive: true, force: true });
-    vi.restoreAllMocks();
+    vi.unstubAllGlobals();
+
+    // Restore original environment
+    if (previousStateDir === undefined) delete process.env.CLAWDBOT_STATE_DIR;
+    else process.env.CLAWDBOT_STATE_DIR = previousStateDir;
+    if (previousAgentDir === undefined) delete process.env.CLAWDBOT_AGENT_DIR;
+    else process.env.CLAWDBOT_AGENT_DIR = previousAgentDir;
+    if (previousPiAgentDir === undefined) delete process.env.PI_CODING_AGENT_DIR;
+    else process.env.PI_CODING_AGENT_DIR = previousPiAgentDir;
+
+    await fs.rm(tmpDir, { recursive: true, force: true });
   });
 
   it("falls back to main agent credentials when secondary agent token is expired and refresh fails", async () => {
@@ -46,7 +60,7 @@ describe("resolveApiKeyForProfile", () => {
         },
       },
     };
-    await fs.promises.writeFile(
+    await fs.writeFile(
       path.join(secondaryAgentDir, "auth-profiles.json"),
       JSON.stringify(secondaryStore),
     );
@@ -64,15 +78,27 @@ describe("resolveApiKeyForProfile", () => {
         },
       },
     };
-    await fs.promises.writeFile(
-      path.join(mainAgentDir, "auth-profiles.json"),
-      JSON.stringify(mainStore),
-    );
+    await fs.writeFile(path.join(mainAgentDir, "auth-profiles.json"), JSON.stringify(mainStore));
 
-    // The secondary agent should fall back to main agent's credentials
-    // when its own token refresh fails
+    // Mock fetch to simulate OAuth refresh failure
+    const fetchSpy = vi.fn(async () => {
+      return new Response(JSON.stringify({ error: "invalid_grant" }), {
+        status: 400,
+        headers: { "Content-Type": "application/json" },
+      });
+    });
+    vi.stubGlobal("fetch", fetchSpy);
+
+    // Load the secondary agent's store (will merge with main agent's store)
+    const loadedSecondaryStore = ensureAuthProfileStore(secondaryAgentDir);
+
+    // Call resolveApiKeyForProfile with the secondary agent's expired credentials
+    // This should:
+    // 1. Try to refresh the expired token (fails due to mocked fetch)
+    // 2. Fall back to main agent's fresh credentials
+    // 3. Copy those credentials to the secondary agent
     const result = await resolveApiKeyForProfile({
-      store: secondaryStore,
+      store: loadedSecondaryStore,
       profileId,
       agentDir: secondaryAgentDir,
     });
@@ -83,11 +109,56 @@ describe("resolveApiKeyForProfile", () => {
 
     // Verify the credentials were copied to the secondary agent
     const updatedSecondaryStore = JSON.parse(
-      await fs.promises.readFile(path.join(secondaryAgentDir, "auth-profiles.json"), "utf8"),
+      await fs.readFile(path.join(secondaryAgentDir, "auth-profiles.json"), "utf8"),
     ) as AuthProfileStore;
     expect(updatedSecondaryStore.profiles[profileId]).toMatchObject({
       access: "fresh-access-token",
       expires: freshTime,
     });
   });
+
+  it("throws error when both secondary and main agent credentials are expired", async () => {
+    const profileId = "anthropic:claude-cli";
+    const now = Date.now();
+    const expiredTime = now - 60 * 60 * 1000; // 1 hour ago
+
+    // Write expired credentials for both agents
+    const expiredStore: AuthProfileStore = {
+      version: 1,
+      profiles: {
+        [profileId]: {
+          type: "oauth",
+          provider: "anthropic",
+          access: "expired-access-token",
+          refresh: "expired-refresh-token",
+          expires: expiredTime,
+        },
+      },
+    };
+    await fs.writeFile(
+      path.join(secondaryAgentDir, "auth-profiles.json"),
+      JSON.stringify(expiredStore),
+    );
+    await fs.writeFile(path.join(mainAgentDir, "auth-profiles.json"), JSON.stringify(expiredStore));
+
+    // Mock fetch to simulate OAuth refresh failure
+    const fetchSpy = vi.fn(async () => {
+      return new Response(JSON.stringify({ error: "invalid_grant" }), {
+        status: 400,
+        headers: { "Content-Type": "application/json" },
+      });
+    });
+    vi.stubGlobal("fetch", fetchSpy);
+
+    const loadedSecondaryStore = ensureAuthProfileStore(secondaryAgentDir);
+
+    // Should throw because both agents have expired credentials
+    await expect(
+      resolveApiKeyForProfile({
+        store: loadedSecondaryStore,
+        profileId,
+        agentDir: secondaryAgentDir,
+      }),
+    ).rejects.toThrow(/OAuth token refresh failed/);
+  });
 });

src/agents/compaction.test.ts

@@ -103,5 +103,47 @@ describe("pruneHistoryForContextShare", () => {
     expect(pruned.droppedChunks).toBe(0);
     expect(pruned.messages.length).toBe(messages.length);
     expect(pruned.keptTokens).toBe(estimateMessagesTokens(messages));
+    expect(pruned.droppedMessagesList).toEqual([]);
+  });
+
+  it("returns droppedMessagesList containing dropped messages", () => {
+    const messages: AgentMessage[] = [
+      makeMessage(1, 4000),
+      makeMessage(2, 4000),
+      makeMessage(3, 4000),
+      makeMessage(4, 4000),
+    ];
+    const maxContextTokens = 2000; // budget is 1000 tokens (50%)
+    const pruned = pruneHistoryForContextShare({
+      messages,
+      maxContextTokens,
+      maxHistoryShare: 0.5,
+      parts: 2,
+    });
+
+    expect(pruned.droppedChunks).toBeGreaterThan(0);
+    expect(pruned.droppedMessagesList.length).toBe(pruned.droppedMessages);
+
+    // All messages accounted for: kept + dropped = original
+    const allIds = [
+      ...pruned.droppedMessagesList.map((m) => m.timestamp),
+      ...pruned.messages.map((m) => m.timestamp),
+    ].sort((a, b) => a - b);
+    const originalIds = messages.map((m) => m.timestamp).sort((a, b) => a - b);
+    expect(allIds).toEqual(originalIds);
+  });
+
+  it("returns empty droppedMessagesList when no pruning needed", () => {
+    const messages: AgentMessage[] = [makeMessage(1, 100)];
+    const pruned = pruneHistoryForContextShare({
+      messages,
+      maxContextTokens: 100_000,
+      maxHistoryShare: 0.5,
+      parts: 2,
+    });
+
+    expect(pruned.droppedChunks).toBe(0);
+    expect(pruned.droppedMessagesList).toEqual([]);
+    expect(pruned.messages.length).toBe(1);
   });
 });

src/agents/compaction.ts

@@ -301,6 +301,7 @@ export function pruneHistoryForContextShare(params: {
   parts?: number;
 }): {
   messages: AgentMessage[];
+  droppedMessagesList: AgentMessage[];
   droppedChunks: number;
   droppedMessages: number;
   droppedTokens: number;
@@ -310,6 +311,7 @@ export function pruneHistoryForContextShare(params: {
   const maxHistoryShare = params.maxHistoryShare ?? 0.5;
   const budgetTokens = Math.max(1, Math.floor(params.maxContextTokens * maxHistoryShare));
   let keptMessages = params.messages;
+  const allDroppedMessages: AgentMessage[] = [];
   let droppedChunks = 0;
   let droppedMessages = 0;
   let droppedTokens = 0;
@@ -323,11 +325,13 @@ export function pruneHistoryForContextShare(params: {
     droppedChunks += 1;
     droppedMessages += dropped.length;
     droppedTokens += estimateMessagesTokens(dropped);
+    allDroppedMessages.push(...dropped);
     keptMessages = rest.flat();
   }
 
   return {
     messages: keptMessages,
+    droppedMessagesList: allDroppedMessages,
     droppedChunks,
     droppedMessages,
     droppedTokens,

src/agents/model-fallback.test.ts

@@ -1,6 +1,13 @@
+import crypto from "node:crypto";
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
 import { describe, expect, it, vi } from "vitest";
 
 import type { ClawdbotConfig } from "../config/config.js";
+import type { AuthProfileStore } from "./auth-profiles.js";
+import { saveAuthProfileStore } from "./auth-profiles.js";
+import { AUTH_STORE_VERSION } from "./auth-profiles/constants.js";
 import { runWithModelFallback } from "./model-fallback.js";
 
 function makeCfg(overrides: Partial<ClawdbotConfig> = {}): ClawdbotConfig {
@@ -117,6 +124,122 @@ describe("runWithModelFallback", () => {
     expect(run.mock.calls[1]?.[1]).toBe("claude-haiku-3-5");
   });
 
+  it("skips providers when all profiles are in cooldown", async () => {
+    const tempDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-auth-"));
+    const provider = `cooldown-test-${crypto.randomUUID()}`;
+    const profileId = `${provider}:default`;
+
+    const store: AuthProfileStore = {
+      version: AUTH_STORE_VERSION,
+      profiles: {
+        [profileId]: {
+          type: "api_key",
+          provider,
+          key: "test-key",
+        },
+      },
+      usageStats: {
+        [profileId]: {
+          cooldownUntil: Date.now() + 60_000,
+        },
+      },
+    };
+
+    saveAuthProfileStore(store, tempDir);
+
+    const cfg = makeCfg({
+      agents: {
+        defaults: {
+          model: {
+            primary: `${provider}/m1`,
+            fallbacks: ["fallback/ok-model"],
+          },
+        },
+      },
+    });
+    const run = vi.fn().mockImplementation(async (providerId, modelId) => {
+      if (providerId === "fallback") return "ok";
+      throw new Error(`unexpected provider: ${providerId}/${modelId}`);
+    });
+
+    try {
+      const result = await runWithModelFallback({
+        cfg,
+        provider,
+        model: "m1",
+        agentDir: tempDir,
+        run,
+      });
+
+      expect(result.result).toBe("ok");
+      expect(run.mock.calls).toEqual([["fallback", "ok-model"]]);
+      expect(result.attempts[0]?.reason).toBe("rate_limit");
+    } finally {
+      await fs.rm(tempDir, { recursive: true, force: true });
+    }
+  });
+
+  it("does not skip when any profile is available", async () => {
+    const tempDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-auth-"));
+    const provider = `cooldown-mixed-${crypto.randomUUID()}`;
+    const profileA = `${provider}:a`;
+    const profileB = `${provider}:b`;
+
+    const store: AuthProfileStore = {
+      version: AUTH_STORE_VERSION,
+      profiles: {
+        [profileA]: {
+          type: "api_key",
+          provider,
+          key: "key-a",
+        },
+        [profileB]: {
+          type: "api_key",
+          provider,
+          key: "key-b",
+        },
+      },
+      usageStats: {
+        [profileA]: {
+          cooldownUntil: Date.now() + 60_000,
+        },
+      },
+    };
+
+    saveAuthProfileStore(store, tempDir);
+
+    const cfg = makeCfg({
+      agents: {
+        defaults: {
+          model: {
+            primary: `${provider}/m1`,
+            fallbacks: ["fallback/ok-model"],
+          },
+        },
+      },
+    });
+    const run = vi.fn().mockImplementation(async (providerId) => {
+      if (providerId === provider) return "ok";
+      return "unexpected";
+    });
+
+    try {
+      const result = await runWithModelFallback({
+        cfg,
+        provider,
+        model: "m1",
+        agentDir: tempDir,
+        run,
+      });
+
+      expect(result.result).toBe("ok");
+      expect(run.mock.calls).toEqual([[provider, "m1"]]);
+      expect(result.attempts).toEqual([]);
+    } finally {
+      await fs.rm(tempDir, { recursive: true, force: true });
+    }
+  });
+
   it("does not append configured primary when fallbacksOverride is set", async () => {
     const cfg = makeCfg({
       agents: {

src/agents/model-fallback.ts

@@ -14,6 +14,11 @@ import {
   resolveModelRefFromString,
 } from "./model-selection.js";
 import type { FailoverReason } from "./pi-embedded-helpers.js";
+import {
+  ensureAuthProfileStore,
+  isProfileInCooldown,
+  resolveAuthProfileOrder,
+} from "./auth-profiles.js";
 
 type ModelCandidate = {
   provider: string;
@@ -189,6 +194,7 @@ export async function runWithModelFallback<T>(params: {
   cfg: ClawdbotConfig | undefined;
   provider: string;
   model: string;
+  agentDir?: string;
   /** Optional explicit fallbacks list; when provided (even empty), replaces agents.defaults.model.fallbacks. */
   fallbacksOverride?: string[];
   run: (provider: string, model: string) => Promise<T>;
@@ -211,11 +217,33 @@ export async function runWithModelFallback<T>(params: {
     model: params.model,
     fallbacksOverride: params.fallbacksOverride,
   });
+  const authStore = params.cfg
+    ? ensureAuthProfileStore(params.agentDir, { allowKeychainPrompt: false })
+    : null;
   const attempts: FallbackAttempt[] = [];
   let lastError: unknown;
 
   for (let i = 0; i < candidates.length; i += 1) {
     const candidate = candidates[i] as ModelCandidate;
+    if (authStore) {
+      const profileIds = resolveAuthProfileOrder({
+        cfg: params.cfg,
+        store: authStore,
+        provider: candidate.provider,
+      });
+      const isAnyProfileAvailable = profileIds.some((id) => !isProfileInCooldown(authStore, id));
+
+      if (profileIds.length > 0 && !isAnyProfileAvailable) {
+        // All profiles for this provider are in cooldown; skip without attempting
+        attempts.push({
+          provider: candidate.provider,
+          model: candidate.model,
+          error: `Provider ${candidate.provider} is in cooldown (all profiles unavailable)`,
+          reason: "rate_limit",
+        });
+        continue;
+      }
+    }
     try {
       const result = await params.run(candidate.provider, candidate.model);
       return {

src/agents/pi-embedded-runner/extensions.ts

@@ -7,6 +7,7 @@ import type { SessionManager } from "@mariozechner/pi-coding-agent";
 import type { ClawdbotConfig } from "../../config/config.js";
 import { resolveContextWindowInfo } from "../context-window-guard.js";
 import { DEFAULT_CONTEXT_TOKENS } from "../defaults.js";
+import { setCompactionSafeguardRuntime } from "../pi-extensions/compaction-safeguard-runtime.js";
 import { setContextPruningRuntime } from "../pi-extensions/context-pruning/runtime.js";
 import { computeEffectiveSettings } from "../pi-extensions/context-pruning/settings.js";
 import { makeToolPrunablePredicate } from "../pi-extensions/context-pruning/tools.js";
@@ -75,6 +76,10 @@ export function buildEmbeddedExtensionPaths(params: {
 }): string[] {
   const paths: string[] = [];
   if (resolveCompactionMode(params.cfg) === "safeguard") {
+    const compactionCfg = params.cfg?.agents?.defaults?.compaction;
+    setCompactionSafeguardRuntime(params.sessionManager, {
+      maxHistoryShare: compactionCfg?.maxHistoryShare,
+    });
     paths.push(resolvePiExtensionPath("compaction-safeguard"));
   }
   const pruning = buildContextPruningExtension(params);

src/agents/pi-extensions/compaction-safeguard-runtime.ts

@@ -0,0 +1,34 @@
+export type CompactionSafeguardRuntimeValue = {
+  maxHistoryShare?: number;
+};
+
+// Session-scoped runtime registry keyed by object identity.
+// Follows the same WeakMap pattern as context-pruning/runtime.ts.
+const REGISTRY = new WeakMap<object, CompactionSafeguardRuntimeValue>();
+
+export function setCompactionSafeguardRuntime(
+  sessionManager: unknown,
+  value: CompactionSafeguardRuntimeValue | null,
+): void {
+  if (!sessionManager || typeof sessionManager !== "object") {
+    return;
+  }
+
+  const key = sessionManager as object;
+  if (value === null) {
+    REGISTRY.delete(key);
+    return;
+  }
+
+  REGISTRY.set(key, value);
+}
+
+export function getCompactionSafeguardRuntime(
+  sessionManager: unknown,
+): CompactionSafeguardRuntimeValue | null {
+  if (!sessionManager || typeof sessionManager !== "object") {
+    return null;
+  }
+
+  return REGISTRY.get(sessionManager as object) ?? null;
+}

src/agents/pi-extensions/compaction-safeguard.test.ts

@@ -1,6 +1,10 @@
 import type { AgentMessage } from "@mariozechner/pi-agent-core";
 import { describe, expect, it } from "vitest";
 
+import {
+  getCompactionSafeguardRuntime,
+  setCompactionSafeguardRuntime,
+} from "./compaction-safeguard-runtime.js";
 import { __testing } from "./compaction-safeguard.js";
 
 const {
@@ -208,3 +212,41 @@ describe("isOversizedForSummary", () => {
     expect(typeof isOversized).toBe("boolean");
   });
 });
+
+describe("compaction-safeguard runtime registry", () => {
+  it("stores and retrieves config by session manager identity", () => {
+    const sm = {};
+    setCompactionSafeguardRuntime(sm, { maxHistoryShare: 0.3 });
+    const runtime = getCompactionSafeguardRuntime(sm);
+    expect(runtime).toEqual({ maxHistoryShare: 0.3 });
+  });
+
+  it("returns null for unknown session manager", () => {
+    const sm = {};
+    expect(getCompactionSafeguardRuntime(sm)).toBeNull();
+  });
+
+  it("clears entry when value is null", () => {
+    const sm = {};
+    setCompactionSafeguardRuntime(sm, { maxHistoryShare: 0.7 });
+    expect(getCompactionSafeguardRuntime(sm)).not.toBeNull();
+    setCompactionSafeguardRuntime(sm, null);
+    expect(getCompactionSafeguardRuntime(sm)).toBeNull();
+  });
+
+  it("ignores non-object session managers", () => {
+    setCompactionSafeguardRuntime(null, { maxHistoryShare: 0.5 });
+    expect(getCompactionSafeguardRuntime(null)).toBeNull();
+    setCompactionSafeguardRuntime(undefined, { maxHistoryShare: 0.5 });
+    expect(getCompactionSafeguardRuntime(undefined)).toBeNull();
+  });
+
+  it("isolates different session managers", () => {
+    const sm1 = {};
+    const sm2 = {};
+    setCompactionSafeguardRuntime(sm1, { maxHistoryShare: 0.3 });
+    setCompactionSafeguardRuntime(sm2, { maxHistoryShare: 0.8 });
+    expect(getCompactionSafeguardRuntime(sm1)).toEqual({ maxHistoryShare: 0.3 });
+    expect(getCompactionSafeguardRuntime(sm2)).toEqual({ maxHistoryShare: 0.8 });
+  });
+});

src/agents/pi-extensions/compaction-safeguard.ts

@@ -11,6 +11,7 @@ import {
   resolveContextWindowTokens,
   summarizeInStages,
 } from "../compaction.js";
+import { getCompactionSafeguardRuntime } from "./compaction-safeguard-runtime.js";
 const FALLBACK_SUMMARY =
   "Summary unavailable due to context limits. Older messages were truncated.";
 const TURN_PREFIX_INSTRUCTIONS =
@@ -174,21 +175,28 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
       const turnPrefixMessages = preparation.turnPrefixMessages ?? [];
       let messagesToSummarize = preparation.messagesToSummarize;
 
+      const runtime = getCompactionSafeguardRuntime(ctx.sessionManager);
+      const maxHistoryShare = runtime?.maxHistoryShare ?? 0.5;
+
       const tokensBefore =
         typeof preparation.tokensBefore === "number" && Number.isFinite(preparation.tokensBefore)
           ? preparation.tokensBefore
           : undefined;
+
+      let droppedSummary: string | undefined;
+
       if (tokensBefore !== undefined) {
         const summarizableTokens =
           estimateMessagesTokens(messagesToSummarize) + estimateMessagesTokens(turnPrefixMessages);
         const newContentTokens = Math.max(0, Math.floor(tokensBefore - summarizableTokens));
-        const maxHistoryTokens = Math.floor(contextWindowTokens * 0.5);
+        // Apply SAFETY_MARGIN so token underestimates don't trigger unnecessary pruning
+        const maxHistoryTokens = Math.floor(contextWindowTokens * maxHistoryShare * SAFETY_MARGIN);
 
         if (newContentTokens > maxHistoryTokens) {
           const pruned = pruneHistoryForContextShare({
             messages: messagesToSummarize,
             maxContextTokens: contextWindowTokens,
-            maxHistoryShare: 0.5,
+            maxHistoryShare,
             parts: 2,
           });
           if (pruned.droppedChunks > 0) {
@@ -200,6 +208,37 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
                 `(${pruned.droppedMessages} messages) to fit history budget.`,
             );
             messagesToSummarize = pruned.messages;
+
+            // Summarize dropped messages so context isn't lost
+            if (pruned.droppedMessagesList.length > 0) {
+              try {
+                const droppedChunkRatio = computeAdaptiveChunkRatio(
+                  pruned.droppedMessagesList,
+                  contextWindowTokens,
+                );
+                const droppedMaxChunkTokens = Math.max(
+                  1,
+                  Math.floor(contextWindowTokens * droppedChunkRatio),
+                );
+                droppedSummary = await summarizeInStages({
+                  messages: pruned.droppedMessagesList,
+                  model,
+                  apiKey,
+                  signal,
+                  reserveTokens: Math.max(1, Math.floor(preparation.settings.reserveTokens)),
+                  maxChunkTokens: droppedMaxChunkTokens,
+                  contextWindow: contextWindowTokens,
+                  customInstructions,
+                  previousSummary: preparation.previousSummary,
+                });
+              } catch (droppedError) {
+                console.warn(
+                  `Compaction safeguard: failed to summarize dropped messages, continuing without: ${
+                    droppedError instanceof Error ? droppedError.message : String(droppedError)
+                  }`,
+                );
+              }
+            }
           }
         }
       }
@@ -210,6 +249,10 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
       const maxChunkTokens = Math.max(1, Math.floor(contextWindowTokens * adaptiveRatio));
       const reserveTokens = Math.max(1, Math.floor(preparation.settings.reserveTokens));
 
+      // Feed dropped-messages summary as previousSummary so the main summarization
+      // incorporates context from pruned messages instead of losing it entirely.
+      const effectivePreviousSummary = droppedSummary ?? preparation.previousSummary;
+
       const historySummary = await summarizeInStages({
         messages: messagesToSummarize,
         model,
@@ -219,7 +262,7 @@ export default function compactionSafeguardExtension(api: ExtensionAPI): void {
         maxChunkTokens,
         contextWindow: contextWindowTokens,
         customInstructions,
-        previousSummary: preparation.previousSummary,
+        previousSummary: effectivePreviousSummary,
       });
 
       let summary = historySummary;

src/auto-reply/reply/agent-runner-execution.ts

@@ -138,6 +138,7 @@ export async function runAgentTurnWithFallback(params: {
         cfg: params.followupRun.run.config,
         provider: params.followupRun.run.provider,
         model: params.followupRun.run.model,
+        agentDir: params.followupRun.run.agentDir,
         fallbacksOverride: resolveAgentModelFallbacksOverride(
           params.followupRun.run.config,
           resolveAgentIdFromSessionKey(params.followupRun.run.sessionKey),

src/auto-reply/reply/agent-runner-memory.ts

@@ -92,6 +92,7 @@ export async function runMemoryFlushIfNeeded(params: {
       cfg: params.followupRun.run.config,
       provider: params.followupRun.run.provider,
       model: params.followupRun.run.model,
+      agentDir: params.followupRun.run.agentDir,
       fallbacksOverride: resolveAgentModelFallbacksOverride(
         params.followupRun.run.config,
         resolveAgentIdFromSessionKey(params.followupRun.run.sessionKey),

src/auto-reply/reply/followup-runner.ts

@@ -129,6 +129,7 @@ export function createFollowupRunner(params: {
           cfg: queued.run.config,
           provider: queued.run.provider,
           model: queued.run.model,
+          agentDir: queued.run.agentDir,
           fallbacksOverride: resolveAgentModelFallbacksOverride(
             queued.run.config,
             resolveAgentIdFromSessionKey(queued.run.sessionKey),

src/commands/agent.ts

@@ -382,6 +382,7 @@ export async function agentCommand(
         cfg,
         provider,
         model,
+        agentDir,
         fallbacksOverride: resolveAgentModelFallbacksOverride(cfg, sessionAgentId),
         run: (providerOverride, modelOverride) => {
           if (isCliProvider(providerOverride, cfg)) {

src/config/types.agent-defaults.ts

@@ -244,6 +244,8 @@ export type AgentCompactionConfig = {
   mode?: AgentCompactionMode;
   /** Minimum reserve tokens enforced for Pi compaction (0 disables the floor). */
   reserveTokensFloor?: number;
+  /** Max share of context window for history during safeguard pruning (0.1–0.9, default 0.5). */
+  maxHistoryShare?: number;
   /** Pre-compaction memory flush (agentic turn). Default: enabled. */
   memoryFlush?: AgentCompactionMemoryFlushConfig;
 };

src/config/zod-schema.agent-defaults.ts

@@ -90,6 +90,7 @@ export const AgentDefaultsSchema = z
       .object({
         mode: z.union([z.literal("default"), z.literal("safeguard")]).optional(),
         reserveTokensFloor: z.number().int().nonnegative().optional(),
+        maxHistoryShare: z.number().min(0.1).max(0.9).optional(),
         memoryFlush: z
           .object({
             enabled: z.boolean().optional(),

src/cron/isolated-agent/run.ts

@@ -1,5 +1,6 @@
 import {
   resolveAgentConfig,
+  resolveAgentDir,
   resolveAgentModelFallbacksOverride,
   resolveAgentWorkspaceDir,
   resolveDefaultAgentId,
@@ -128,6 +129,7 @@ export async function runCronIsolatedAgentTurn(params: {
   });
 
   const workspaceDirRaw = resolveAgentWorkspaceDir(params.cfg, agentId);
+  const agentDir = resolveAgentDir(params.cfg, agentId);
   const workspace = await ensureAgentWorkspace({
     dir: workspaceDirRaw,
     ensureBootstrapFiles: !agentCfg?.skipBootstrap,
@@ -330,6 +332,7 @@ export async function runCronIsolatedAgentTurn(params: {
       cfg: cfgWithAgentDefaults,
       provider,
       model,
+      agentDir,
       fallbacksOverride: resolveAgentModelFallbacksOverride(params.cfg, agentId),
       run: (providerOverride, modelOverride) => {
         if (isCliProvider(providerOverride, cfgWithAgentDefaults)) {

src/telegram/api-logging.ts

@@ -0,0 +1,41 @@
+import { danger } from "../globals.js";
+import { formatErrorMessage } from "../infra/errors.js";
+import { createSubsystemLogger } from "../logging/subsystem.js";
+import type { RuntimeEnv } from "../runtime.js";
+
+export type TelegramApiLogger = (message: string) => void;
+
+type TelegramApiLoggingParams<T> = {
+  operation: string;
+  fn: () => Promise<T>;
+  runtime?: RuntimeEnv;
+  logger?: TelegramApiLogger;
+  shouldLog?: (err: unknown) => boolean;
+};
+
+const fallbackLogger = createSubsystemLogger("telegram/api");
+
+function resolveTelegramApiLogger(runtime?: RuntimeEnv, logger?: TelegramApiLogger) {
+  if (logger) return logger;
+  if (runtime?.error) return runtime.error;
+  return (message: string) => fallbackLogger.error(message);
+}
+
+export async function withTelegramApiErrorLogging<T>({
+  operation,
+  fn,
+  runtime,
+  logger,
+  shouldLog,
+}: TelegramApiLoggingParams<T>): Promise<T> {
+  try {
+    return await fn();
+  } catch (err) {
+    if (!shouldLog || shouldLog(err)) {
+      const errText = formatErrorMessage(err);
+      const log = resolveTelegramApiLogger(runtime, logger);
+      log(danger(`telegram ${operation} failed: ${errText}`));
+    }
+    throw err;
+  }
+}

src/telegram/bot-handlers.ts

@@ -8,6 +8,7 @@ import { loadConfig } from "../config/config.js";
 import { writeConfigFile } from "../config/io.js";
 import { danger, logVerbose, warn } from "../globals.js";
 import { resolveMedia } from "./bot/delivery.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 import { resolveTelegramForumThreadId } from "./bot/helpers.js";
 import type { TelegramMessage } from "./bot/types.js";
 import { firstDefined, isSenderAllowed, normalizeAllowFromWithStore } from "./bot-access.js";
@@ -180,7 +181,11 @@ export const registerTelegramHandlers = ({
     if (!callback) return;
     if (shouldSkipUpdate(ctx)) return;
     // Answer immediately to prevent Telegram from retrying while we process
-    await bot.api.answerCallbackQuery(callback.id).catch(() => {});
+    await withTelegramApiErrorLogging({
+      operation: "answerCallbackQuery",
+      runtime,
+      fn: () => bot.api.answerCallbackQuery(callback.id),
+    }).catch(() => {});
     try {
       const data = (callback.data ?? "").trim();
       const callbackMessage = callback.message;
@@ -577,11 +582,14 @@ export const registerTelegramHandlers = ({
         const errMsg = String(mediaErr);
         if (errMsg.includes("exceeds") && errMsg.includes("MB limit")) {
           const limitMb = Math.round(mediaMaxBytes / (1024 * 1024));
-          await bot.api
-            .sendMessage(chatId, `⚠️ File too large. Maximum size is ${limitMb}MB.`, {
-              reply_to_message_id: msg.message_id,
-            })
-            .catch(() => {});
+          await withTelegramApiErrorLogging({
+            operation: "sendMessage",
+            runtime,
+            fn: () =>
+              bot.api.sendMessage(chatId, `⚠️ File too large. Maximum size is ${limitMb}MB.`, {
+                reply_to_message_id: msg.message_id,
+              }),
+          }).catch(() => {});
           logger.warn({ chatId, error: errMsg }, "media exceeds size limit");
           return;
         }

src/telegram/bot-message-context.ts

@@ -25,6 +25,7 @@ import { shouldAckReaction as shouldAckReactionGate } from "../channels/ack-reac
 import { resolveMentionGatingWithBypass } from "../channels/mention-gating.js";
 import { resolveControlCommandGate } from "../channels/command-gating.js";
 import { logInboundDrop } from "../channels/logging.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 import {
   buildGroupLabel,
   buildSenderLabel,
@@ -165,16 +166,19 @@ export const buildTelegramMessageContext = async ({
   }
 
   const sendTyping = async () => {
-    await bot.api.sendChatAction(chatId, "typing", buildTypingThreadParams(resolvedThreadId));
+    await withTelegramApiErrorLogging({
+      operation: "sendChatAction",
+      fn: () => bot.api.sendChatAction(chatId, "typing", buildTypingThreadParams(resolvedThreadId)),
+    });
   };
 
   const sendRecordVoice = async () => {
     try {
-      await bot.api.sendChatAction(
-        chatId,
-        "record_voice",
-        buildTypingThreadParams(resolvedThreadId),
-      );
+      await withTelegramApiErrorLogging({
+        operation: "sendChatAction",
+        fn: () =>
+          bot.api.sendChatAction(chatId, "record_voice", buildTypingThreadParams(resolvedThreadId)),
+      });
     } catch (err) {
       logVerbose(`telegram record_voice cue failed for chat ${chatId}: ${String(err)}`);
     }
@@ -227,19 +231,23 @@ export const buildTelegramMessageContext = async ({
                 },
                 "telegram pairing request",
               );
-              await bot.api.sendMessage(
-                chatId,
-                [
-                  "Clawdbot: access not configured.",
-                  "",
-                  `Your Telegram user id: ${telegramUserId}`,
-                  "",
-                  `Pairing code: ${code}`,
-                  "",
-                  "Ask the bot owner to approve with:",
-                  formatCliCommand("clawdbot pairing approve telegram <code>"),
-                ].join("\n"),
-              );
+              await withTelegramApiErrorLogging({
+                operation: "sendMessage",
+                fn: () =>
+                  bot.api.sendMessage(
+                    chatId,
+                    [
+                      "Clawdbot: access not configured.",
+                      "",
+                      `Your Telegram user id: ${telegramUserId}`,
+                      "",
+                      `Pairing code: ${code}`,
+                      "",
+                      "Ask the bot owner to approve with:",
+                      formatCliCommand("clawdbot pairing approve telegram <code>"),
+                    ].join("\n"),
+                  ),
+              });
             }
           } catch (err) {
             logVerbose(`telegram pairing reply failed for chat ${chatId}: ${String(err)}`);
@@ -408,7 +416,10 @@ export const buildTelegramMessageContext = async ({
     typeof api.setMessageReaction === "function" ? api.setMessageReaction.bind(api) : null;
   const ackReactionPromise =
     shouldAckReaction() && msg.message_id && reactionApi
-      ? reactionApi(chatId, msg.message_id, [{ type: "emoji", emoji: ackReaction }]).then(
+      ? withTelegramApiErrorLogging({
+          operation: "setMessageReaction",
+          fn: () => reactionApi(chatId, msg.message_id, [{ type: "emoji", emoji: ackReaction }]),
+        }).then(
           () => true,
           (err) => {
             logVerbose(`telegram react failed for chat ${chatId}: ${String(err)}`);

src/telegram/bot-native-commands.ts

@@ -17,6 +17,7 @@ import { dispatchReplyWithBufferedBlockDispatcher } from "../auto-reply/reply/pr
 import { finalizeInboundContext } from "../auto-reply/reply/inbound-context.js";
 import { danger, logVerbose } from "../globals.js";
 import { resolveMarkdownTableMode } from "../config/markdown-tables.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 import {
   normalizeTelegramCommandName,
   TELEGRAM_COMMAND_NAME_PATTERN,
@@ -134,11 +135,17 @@ async function resolveTelegramCommandAuth(params: {
   const senderUsername = msg.from?.username ?? "";
 
   if (isGroup && groupConfig?.enabled === false) {
-    await bot.api.sendMessage(chatId, "This group is disabled.");
+    await withTelegramApiErrorLogging({
+      operation: "sendMessage",
+      fn: () => bot.api.sendMessage(chatId, "This group is disabled."),
+    });
     return null;
   }
   if (isGroup && topicConfig?.enabled === false) {
-    await bot.api.sendMessage(chatId, "This topic is disabled.");
+    await withTelegramApiErrorLogging({
+      operation: "sendMessage",
+      fn: () => bot.api.sendMessage(chatId, "This topic is disabled."),
+    });
     return null;
   }
   if (requireAuth && isGroup && hasGroupAllowOverride) {
@@ -150,7 +157,10 @@ async function resolveTelegramCommandAuth(params: {
         senderUsername,
       })
     ) {
-      await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
+      await withTelegramApiErrorLogging({
+        operation: "sendMessage",
+        fn: () => bot.api.sendMessage(chatId, "You are not authorized to use this command."),
+      });
       return null;
     }
   }
@@ -159,7 +169,10 @@ async function resolveTelegramCommandAuth(params: {
     const defaultGroupPolicy = cfg.channels?.defaults?.groupPolicy;
     const groupPolicy = telegramCfg.groupPolicy ?? defaultGroupPolicy ?? "open";
     if (groupPolicy === "disabled") {
-      await bot.api.sendMessage(chatId, "Telegram group commands are disabled.");
+      await withTelegramApiErrorLogging({
+        operation: "sendMessage",
+        fn: () => bot.api.sendMessage(chatId, "Telegram group commands are disabled."),
+      });
       return null;
     }
     if (groupPolicy === "allowlist" && requireAuth) {
@@ -171,13 +184,19 @@ async function resolveTelegramCommandAuth(params: {
           senderUsername,
         })
       ) {
-        await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
+        await withTelegramApiErrorLogging({
+          operation: "sendMessage",
+          fn: () => bot.api.sendMessage(chatId, "You are not authorized to use this command."),
+        });
         return null;
       }
     }
     const groupAllowlist = resolveGroupPolicy(chatId);
     if (groupAllowlist.allowlistEnabled && !groupAllowlist.allowed) {
-      await bot.api.sendMessage(chatId, "This group is not allowed.");
+      await withTelegramApiErrorLogging({
+        operation: "sendMessage",
+        fn: () => bot.api.sendMessage(chatId, "This group is not allowed."),
+      });
       return null;
     }
   }
@@ -197,7 +216,10 @@ async function resolveTelegramCommandAuth(params: {
     modeWhenAccessGroupsOff: "configured",
   });
   if (requireAuth && !commandAuthorized) {
-    await bot.api.sendMessage(chatId, "You are not authorized to use this command.");
+    await withTelegramApiErrorLogging({
+      operation: "sendMessage",
+      fn: () => bot.api.sendMessage(chatId, "You are not authorized to use this command."),
+    });
     return null;
   }
 
@@ -300,9 +322,11 @@ export const registerTelegramNativeCommands = ({
   ];
 
   if (allCommands.length > 0) {
-    bot.api.setMyCommands(allCommands).catch((err) => {
-      runtime.error?.(danger(`telegram setMyCommands failed: ${String(err)}`));
-    });
+    void withTelegramApiErrorLogging({
+      operation: "setMyCommands",
+      runtime,
+      fn: () => bot.api.setMyCommands(allCommands),
+    }).catch(() => {});
 
     if (typeof (bot as unknown as { command?: unknown }).command !== "function") {
       logVerbose("telegram: bot.command unavailable; skipping native handlers");
@@ -376,9 +400,14 @@ export const registerTelegramNativeCommands = ({
               );
             }
             const replyMarkup = buildInlineKeyboard(rows);
-            await bot.api.sendMessage(chatId, title, {
-              ...(replyMarkup ? { reply_markup: replyMarkup } : {}),
-              ...(resolvedThreadId != null ? { message_thread_id: resolvedThreadId } : {}),
+            await withTelegramApiErrorLogging({
+              operation: "sendMessage",
+              runtime,
+              fn: () =>
+                bot.api.sendMessage(chatId, title, {
+                  ...(replyMarkup ? { reply_markup: replyMarkup } : {}),
+                  ...(resolvedThreadId != null ? { message_thread_id: resolvedThreadId } : {}),
+                }),
             });
             return;
           }
@@ -492,7 +521,11 @@ export const registerTelegramNativeCommands = ({
           const commandBody = `/${pluginCommand.command}${rawText ? ` ${rawText}` : ""}`;
           const match = matchPluginCommand(commandBody);
           if (!match) {
-            await bot.api.sendMessage(chatId, "Command not found.");
+            await withTelegramApiErrorLogging({
+              operation: "sendMessage",
+              runtime,
+              fn: () => bot.api.sendMessage(chatId, "Command not found."),
+            });
             return;
           }
           const auth = await resolveTelegramCommandAuth({
@@ -543,8 +576,10 @@ export const registerTelegramNativeCommands = ({
       }
     }
   } else if (nativeDisabledExplicit) {
-    bot.api.setMyCommands([]).catch((err) => {
-      runtime.error?.(danger(`telegram clear commands failed: ${String(err)}`));
-    });
+    void withTelegramApiErrorLogging({
+      operation: "setMyCommands",
+      runtime,
+      fn: () => bot.api.setMyCommands([]),
+    }).catch(() => {});
   }
 };

src/telegram/bot.ts

@@ -24,6 +24,7 @@ import { createSubsystemLogger } from "../logging/subsystem.js";
 import { formatUncaughtError } from "../infra/errors.js";
 import { enqueueSystemEvent } from "../infra/system-events.js";
 import { getChildLogger } from "../logging.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 import { resolveAgentRoute } from "../routing/resolve-route.js";
 import { resolveThreadSessionKeys } from "../routing/session-key.js";
 import type { RuntimeEnv } from "../runtime.js";
@@ -261,7 +262,11 @@ export function createTelegramBot(opts: TelegramBotOptions) {
     }
     if (typeof botHasTopicsEnabled === "boolean") return botHasTopicsEnabled;
     try {
-      const me = (await bot.api.getMe()) as { has_topics_enabled?: boolean };
+      const me = (await withTelegramApiErrorLogging({
+        operation: "getMe",
+        runtime,
+        fn: () => bot.api.getMe(),
+      })) as { has_topics_enabled?: boolean };
       botHasTopicsEnabled = Boolean(me?.has_topics_enabled);
     } catch (err) {
       logVerbose(`telegram getMe failed: ${String(err)}`);

src/telegram/bot/delivery.ts

@@ -4,6 +4,7 @@ import {
   markdownToTelegramHtml,
   renderTelegramHtmlText,
 } from "../format.js";
+import { withTelegramApiErrorLogging } from "../api-logging.js";
 import { chunkMarkdownTextWithMode, type ChunkMode } from "../../auto-reply/chunk.js";
 import { splitTelegramCaption } from "../caption.js";
 import type { ReplyPayload } from "../../auto-reply/types.js";
@@ -25,24 +26,6 @@ import type { TelegramContext } from "./types.js";
 const PARSE_ERR_RE = /can't parse entities|parse entities|find end of the entity/i;
 const VOICE_FORBIDDEN_RE = /VOICE_MESSAGES_FORBIDDEN/;
 
-/**
- * Wraps a Telegram API call with error logging. Ensures network failures are
- * logged with context before propagating, preventing silent unhandled rejections.
- */
-async function withMediaErrorHandler<T>(
-  operation: string,
-  runtime: RuntimeEnv,
-  fn: () => Promise<T>,
-): Promise<T> {
-  try {
-    return await fn();
-  } catch (err) {
-    const errText = formatErrorMessage(err);
-    runtime.error?.(danger(`telegram ${operation} failed: ${errText}`));
-    throw err;
-  }
-}
-
 export async function deliverReplies(params: {
   replies: ReplyPayload[];
   chatId: string;
@@ -164,17 +147,23 @@ export async function deliverReplies(params: {
         mediaParams.message_thread_id = threadParams.message_thread_id;
       }
       if (isGif) {
-        await withMediaErrorHandler("sendAnimation", runtime, () =>
-          bot.api.sendAnimation(chatId, file, { ...mediaParams }),
-        );
+        await withTelegramApiErrorLogging({
+          operation: "sendAnimation",
+          runtime,
+          fn: () => bot.api.sendAnimation(chatId, file, { ...mediaParams }),
+        });
       } else if (kind === "image") {
-        await withMediaErrorHandler("sendPhoto", runtime, () =>
-          bot.api.sendPhoto(chatId, file, { ...mediaParams }),
-        );
+        await withTelegramApiErrorLogging({
+          operation: "sendPhoto",
+          runtime,
+          fn: () => bot.api.sendPhoto(chatId, file, { ...mediaParams }),
+        });
       } else if (kind === "video") {
-        await withMediaErrorHandler("sendVideo", runtime, () =>
-          bot.api.sendVideo(chatId, file, { ...mediaParams }),
-        );
+        await withTelegramApiErrorLogging({
+          operation: "sendVideo",
+          runtime,
+          fn: () => bot.api.sendVideo(chatId, file, { ...mediaParams }),
+        });
       } else if (kind === "audio") {
         const { useVoice } = resolveTelegramVoiceSend({
           wantsVoice: reply.audioAsVoice === true, // default false (backward compatible)
@@ -187,9 +176,12 @@ export async function deliverReplies(params: {
           // Switch typing indicator to record_voice before sending.
           await params.onVoiceRecording?.();
           try {
-            await withMediaErrorHandler("sendVoice", runtime, () =>
-              bot.api.sendVoice(chatId, file, { ...mediaParams }),
-            );
+            await withTelegramApiErrorLogging({
+              operation: "sendVoice",
+              runtime,
+              shouldLog: (err) => !isVoiceMessagesForbidden(err),
+              fn: () => bot.api.sendVoice(chatId, file, { ...mediaParams }),
+            });
           } catch (voiceErr) {
             // Fall back to text if voice messages are forbidden in this chat.
             // This happens when the recipient has Telegram Premium privacy settings
@@ -222,14 +214,18 @@ export async function deliverReplies(params: {
           }
         } else {
           // Audio file - displays with metadata (title, duration) - DEFAULT
-          await withMediaErrorHandler("sendAudio", runtime, () =>
-            bot.api.sendAudio(chatId, file, { ...mediaParams }),
-          );
+          await withTelegramApiErrorLogging({
+            operation: "sendAudio",
+            runtime,
+            fn: () => bot.api.sendAudio(chatId, file, { ...mediaParams }),
+          });
         }
       } else {
-        await withMediaErrorHandler("sendDocument", runtime, () =>
-          bot.api.sendDocument(chatId, file, { ...mediaParams }),
-        );
+        await withTelegramApiErrorLogging({
+          operation: "sendDocument",
+          runtime,
+          fn: () => bot.api.sendDocument(chatId, file, { ...mediaParams }),
+        });
       }
       if (replyToId && !hasReplied) {
         hasReplied = true;
@@ -371,11 +367,17 @@ async function sendTelegramText(
   const textMode = opts?.textMode ?? "markdown";
   const htmlText = textMode === "html" ? text : markdownToTelegramHtml(text);
   try {
-    const res = await bot.api.sendMessage(chatId, htmlText, {
-      parse_mode: "HTML",
-      ...(linkPreviewOptions ? { link_preview_options: linkPreviewOptions } : {}),
-      ...(opts?.replyMarkup ? { reply_markup: opts.replyMarkup } : {}),
-      ...baseParams,
+    const res = await withTelegramApiErrorLogging({
+      operation: "sendMessage",
+      runtime,
+      shouldLog: (err) => !PARSE_ERR_RE.test(formatErrorMessage(err)),
+      fn: () =>
+        bot.api.sendMessage(chatId, htmlText, {
+          parse_mode: "HTML",
+          ...(linkPreviewOptions ? { link_preview_options: linkPreviewOptions } : {}),
+          ...(opts?.replyMarkup ? { reply_markup: opts.replyMarkup } : {}),
+          ...baseParams,
+        }),
     });
     return res.message_id;
   } catch (err) {
@@ -383,10 +385,15 @@ async function sendTelegramText(
     if (PARSE_ERR_RE.test(errText)) {
       runtime.log?.(`telegram HTML parse failed; retrying without formatting: ${errText}`);
       const fallbackText = opts?.plainText ?? text;
-      const res = await bot.api.sendMessage(chatId, fallbackText, {
-        ...(linkPreviewOptions ? { link_preview_options: linkPreviewOptions } : {}),
-        ...(opts?.replyMarkup ? { reply_markup: opts.replyMarkup } : {}),
-        ...baseParams,
+      const res = await withTelegramApiErrorLogging({
+        operation: "sendMessage",
+        runtime,
+        fn: () =>
+          bot.api.sendMessage(chatId, fallbackText, {
+            ...(linkPreviewOptions ? { link_preview_options: linkPreviewOptions } : {}),
+            ...(opts?.replyMarkup ? { reply_markup: opts.replyMarkup } : {}),
+            ...baseParams,
+          }),
       });
       return res.message_id;
     }

src/telegram/send.ts

@@ -8,6 +8,7 @@ import { type ApiClientOptions, Bot, HttpError, InputFile } from "grammy";
 import { loadConfig } from "../config/config.js";
 import { logVerbose } from "../globals.js";
 import { recordChannelActivity } from "../infra/channel-activity.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 import { formatErrorMessage, formatUncaughtError } from "../infra/errors.js";
 import { isDiagnosticFlagEnabled } from "../infra/diagnostic-flags.js";
 import type { RetryConfig } from "../infra/retry.js";
@@ -210,7 +211,10 @@ export async function sendMessageTelegram(
   });
   const logHttpError = createTelegramHttpLogger(cfg);
   const requestWithDiag = <T>(fn: () => Promise<T>, label?: string) =>
-    request(fn, label).catch((err) => {
+    withTelegramApiErrorLogging({
+      operation: label ?? "request",
+      fn: () => request(fn, label),
+    }).catch((err) => {
       logHttpError(label ?? "request", err);
       throw err;
     });
@@ -442,7 +446,10 @@ export async function reactMessageTelegram(
   });
   const logHttpError = createTelegramHttpLogger(cfg);
   const requestWithDiag = <T>(fn: () => Promise<T>, label?: string) =>
-    request(fn, label).catch((err) => {
+    withTelegramApiErrorLogging({
+      operation: label ?? "request",
+      fn: () => request(fn, label),
+    }).catch((err) => {
       logHttpError(label ?? "request", err);
       throw err;
     });
@@ -492,7 +499,10 @@ export async function deleteMessageTelegram(
   });
   const logHttpError = createTelegramHttpLogger(cfg);
   const requestWithDiag = <T>(fn: () => Promise<T>, label?: string) =>
-    request(fn, label).catch((err) => {
+    withTelegramApiErrorLogging({
+      operation: label ?? "request",
+      fn: () => request(fn, label),
+    }).catch((err) => {
       logHttpError(label ?? "request", err);
       throw err;
     });
@@ -537,7 +547,10 @@ export async function editMessageTelegram(
   });
   const logHttpError = createTelegramHttpLogger(cfg);
   const requestWithDiag = <T>(fn: () => Promise<T>, label?: string) =>
-    request(fn, label).catch((err) => {
+    withTelegramApiErrorLogging({
+      operation: label ?? "request",
+      fn: () => request(fn, label),
+    }).catch((err) => {
       logHttpError(label ?? "request", err);
       throw err;
     });

src/telegram/webhook-set.ts

@@ -1,6 +1,7 @@
 import { type ApiClientOptions, Bot } from "grammy";
 import type { TelegramNetworkConfig } from "../config/types.telegram.js";
 import { resolveTelegramFetch } from "./fetch.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 
 export async function setTelegramWebhook(opts: {
   token: string;
@@ -14,9 +15,13 @@ export async function setTelegramWebhook(opts: {
     ? { fetch: fetchImpl as unknown as ApiClientOptions["fetch"] }
     : undefined;
   const bot = new Bot(opts.token, client ? { client } : undefined);
-  await bot.api.setWebhook(opts.url, {
-    secret_token: opts.secret,
-    drop_pending_updates: opts.dropPendingUpdates ?? false,
+  await withTelegramApiErrorLogging({
+    operation: "setWebhook",
+    fn: () =>
+      bot.api.setWebhook(opts.url, {
+        secret_token: opts.secret,
+        drop_pending_updates: opts.dropPendingUpdates ?? false,
+      }),
   });
 }
 
@@ -29,5 +34,8 @@ export async function deleteTelegramWebhook(opts: {
     ? { fetch: fetchImpl as unknown as ApiClientOptions["fetch"] }
     : undefined;
   const bot = new Bot(opts.token, client ? { client } : undefined);
-  await bot.api.deleteWebhook();
+  await withTelegramApiErrorLogging({
+    operation: "deleteWebhook",
+    fn: () => bot.api.deleteWebhook(),
+  });
 }

src/telegram/webhook.ts

@@ -15,6 +15,7 @@ import {
 } from "../logging/diagnostic.js";
 import { resolveTelegramAllowedUpdates } from "./allowed-updates.js";
 import { createTelegramBot } from "./bot.js";
+import { withTelegramApiErrorLogging } from "./api-logging.js";
 
 export async function startTelegramWebhook(opts: {
   token: string;
@@ -97,9 +98,14 @@ export async function startTelegramWebhook(opts: {
   const publicUrl =
     opts.publicUrl ?? `http://${host === "0.0.0.0" ? "localhost" : host}:${port}${path}`;
 
-  await bot.api.setWebhook(publicUrl, {
-    secret_token: opts.secret,
-    allowed_updates: resolveTelegramAllowedUpdates(),
+  await withTelegramApiErrorLogging({
+    operation: "setWebhook",
+    runtime,
+    fn: () =>
+      bot.api.setWebhook(publicUrl, {
+        secret_token: opts.secret,
+        allowed_updates: resolveTelegramAllowedUpdates(),
+      }),
   });
 
   await new Promise<void>((resolve) => server.listen(port, host, resolve));