diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4788e8446..f695aa2f8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -105,6 +105,7 @@
 - Telegram: support media groups (multi-image messages). Thanks @obviyus for PR #220.
 - Telegram/WhatsApp: parse shared locations (pins, places, live) and expose structured ctx fields. Thanks @nachoiacovino for PR #194.
 - Auto-reply: block unauthorized `/reset` and infer WhatsApp senders from E.164 inputs.
+- Auto-reply: reset corrupted Gemini sessions when function-call ordering breaks. Thanks @VACInc for PR #297.
 - Auto-reply: track compaction count in session status; verbose mode announces auto-compactions.
 - Telegram: notify users when inbound media exceeds size limits. Thanks @jarvis-medmatic for PR #283.
 - Telegram: send GIF media as animations (auto-play) and improve filename sniffing.
diff --git a/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts b/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts
index 017a51ca9..5ae3b6ec1 100644
--- a/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts
+++ b/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts
@@ -4,6 +4,7 @@ import path from "node:path";
 import { describe, expect, it, vi } from "vitest";
 
 import type { SessionEntry } from "../../config/sessions.js";
+import * as sessions from "../../config/sessions.js";
 import type { TemplateContext } from "../templating.js";
 import type { GetReplyOptions } from "../types.js";
 import type { FollowupRun, QueueSettings } from "./queue.js";
@@ -209,6 +210,151 @@ describe("runReplyAgent typing (heartbeat)", () => {
     expect(payloads[0]?.text).toContain("count 1");
     expect(sessionStore.main.compactionCount).toBe(1);
   });
+  it("resets corrupted Gemini sessions and deletes transcripts", async () => {
+    const prevStateDir = process.env.CLAWDBOT_STATE_DIR;
+    const stateDir = await fs.mkdtemp(
+      path.join(tmpdir(), "clawdbot-session-reset-"),
+    );
+    process.env.CLAWDBOT_STATE_DIR = stateDir;
+    try {
+      const sessionId = "session-corrupt";
+      const storePath = path.join(stateDir, "sessions", "sessions.json");
+      const sessionEntry = { sessionId, updatedAt: Date.now() };
+      const sessionStore = { main: sessionEntry };
+
+      await fs.mkdir(path.dirname(storePath), { recursive: true });
+      await fs.writeFile(storePath, JSON.stringify(sessionStore), "utf-8");
+
+      const transcriptPath = sessions.resolveSessionTranscriptPath(sessionId);
+      await fs.mkdir(path.dirname(transcriptPath), { recursive: true });
+      await fs.writeFile(transcriptPath, "bad", "utf-8");
+
+      runEmbeddedPiAgentMock.mockImplementationOnce(async () => {
+        throw new Error(
+          "function call turn comes immediately after a user turn or after a function response turn",
+        );
+      });
+
+      const { run } = createMinimalRun({
+        sessionEntry,
+        sessionStore,
+        sessionKey: "main",
+        storePath,
+      });
+      const res = await run();
+
+      expect(res).toMatchObject({
+        text: expect.stringContaining("Session history was corrupted"),
+      });
+      expect(sessionStore.main).toBeUndefined();
+      await expect(fs.access(transcriptPath)).rejects.toThrow();
+
+      const persisted = JSON.parse(await fs.readFile(storePath, "utf-8"));
+      expect(persisted.main).toBeUndefined();
+    } finally {
+      if (prevStateDir) {
+        process.env.CLAWDBOT_STATE_DIR = prevStateDir;
+      } else {
+        delete process.env.CLAWDBOT_STATE_DIR;
+      }
+    }
+  });
+
+  it("keeps sessions intact on other errors", async () => {
+    const prevStateDir = process.env.CLAWDBOT_STATE_DIR;
+    const stateDir = await fs.mkdtemp(
+      path.join(tmpdir(), "clawdbot-session-noreset-"),
+    );
+    process.env.CLAWDBOT_STATE_DIR = stateDir;
+    try {
+      const sessionId = "session-ok";
+      const storePath = path.join(stateDir, "sessions", "sessions.json");
+      const sessionEntry = { sessionId, updatedAt: Date.now() };
+      const sessionStore = { main: sessionEntry };
+
+      await fs.mkdir(path.dirname(storePath), { recursive: true });
+      await fs.writeFile(storePath, JSON.stringify(sessionStore), "utf-8");
+
+      const transcriptPath = sessions.resolveSessionTranscriptPath(sessionId);
+      await fs.mkdir(path.dirname(transcriptPath), { recursive: true });
+      await fs.writeFile(transcriptPath, "ok", "utf-8");
+
+      runEmbeddedPiAgentMock.mockImplementationOnce(async () => {
+        throw new Error("INVALID_ARGUMENT: some other failure");
+      });
+
+      const { run } = createMinimalRun({
+        sessionEntry,
+        sessionStore,
+        sessionKey: "main",
+        storePath,
+      });
+      const res = await run();
+
+      expect(res).toMatchObject({
+        text: expect.stringContaining("Agent failed before reply"),
+      });
+      expect(sessionStore.main).toBeDefined();
+      await expect(fs.access(transcriptPath)).resolves.toBeUndefined();
+
+      const persisted = JSON.parse(await fs.readFile(storePath, "utf-8"));
+      expect(persisted.main).toBeDefined();
+    } finally {
+      if (prevStateDir) {
+        process.env.CLAWDBOT_STATE_DIR = prevStateDir;
+      } else {
+        delete process.env.CLAWDBOT_STATE_DIR;
+      }
+    }
+  });
+
+  it("still replies even if session reset fails to persist", async () => {
+    const prevStateDir = process.env.CLAWDBOT_STATE_DIR;
+    const stateDir = await fs.mkdtemp(
+      path.join(tmpdir(), "clawdbot-session-reset-fail-"),
+    );
+    process.env.CLAWDBOT_STATE_DIR = stateDir;
+    const saveSpy = vi
+      .spyOn(sessions, "saveSessionStore")
+      .mockRejectedValueOnce(new Error("boom"));
+    try {
+      const sessionId = "session-corrupt";
+      const storePath = path.join(stateDir, "sessions", "sessions.json");
+      const sessionEntry = { sessionId, updatedAt: Date.now() };
+      const sessionStore = { main: sessionEntry };
+
+      const transcriptPath = sessions.resolveSessionTranscriptPath(sessionId);
+      await fs.mkdir(path.dirname(transcriptPath), { recursive: true });
+      await fs.writeFile(transcriptPath, "bad", "utf-8");
+
+      runEmbeddedPiAgentMock.mockImplementationOnce(async () => {
+        throw new Error(
+          "function call turn comes immediately after a user turn or after a function response turn",
+        );
+      });
+
+      const { run } = createMinimalRun({
+        sessionEntry,
+        sessionStore,
+        sessionKey: "main",
+        storePath,
+      });
+      const res = await run();
+
+      expect(res).toMatchObject({
+        text: expect.stringContaining("Session history was corrupted"),
+      });
+      expect(sessionStore.main).toBeUndefined();
+      await expect(fs.access(transcriptPath)).rejects.toThrow();
+    } finally {
+      saveSpy.mockRestore();
+      if (prevStateDir) {
+        process.env.CLAWDBOT_STATE_DIR = prevStateDir;
+      } else {
+        delete process.env.CLAWDBOT_STATE_DIR;
+      }
+    }
+  });
 
   it("rewrites Bun socket errors into friendly text", async () => {
     runEmbeddedPiAgentMock.mockImplementationOnce(async () => ({
diff --git a/src/auto-reply/reply/agent-runner.ts b/src/auto-reply/reply/agent-runner.ts
index 79b85e57a..490b696cd 100644
--- a/src/auto-reply/reply/agent-runner.ts
+++ b/src/auto-reply/reply/agent-runner.ts
@@ -1,4 +1,5 @@
 import crypto from "node:crypto";
+import fs from "node:fs";
 import { lookupContextTokens } from "../../agents/context.js";
 import { DEFAULT_CONTEXT_TOKENS } from "../../agents/defaults.js";
 import { runWithModelFallback } from "../../agents/model-fallback.js";
@@ -9,6 +10,7 @@ import {
 import { hasNonzeroUsage } from "../../agents/usage.js";
 import {
   loadSessionStore,
+  resolveSessionTranscriptPath,
   type SessionEntry,
   saveSessionStore,
 } from "../../config/sessions.js";
@@ -378,6 +380,42 @@ export async function runReplyAgent(params: {
       const message = err instanceof Error ? err.message : String(err);
       const isContextOverflow =
         /context.*overflow|too large|context window/i.test(message);
+      const isSessionCorruption =
+        /function call turn comes immediately after/i.test(message);
+
+      // Auto-recover from Gemini session corruption by resetting the session
+      if (isSessionCorruption && sessionKey && sessionStore && storePath) {
+        const corruptedSessionId = sessionEntry?.sessionId;
+        defaultRuntime.error(
+          `Session history corrupted (Gemini function call ordering). Resetting session: ${sessionKey}`,
+        );
+
+        try {
+          // Delete transcript file if it exists
+          if (corruptedSessionId) {
+            const transcriptPath =
+              resolveSessionTranscriptPath(corruptedSessionId);
+            try {
+              fs.unlinkSync(transcriptPath);
+            } catch {
+              // Ignore if file doesn't exist
+            }
+          }
+
+          // Remove session entry from store
+          delete sessionStore[sessionKey];
+          await saveSessionStore(storePath, sessionStore);
+        } catch (cleanupErr) {
+          defaultRuntime.error(
+            `Failed to reset corrupted session ${sessionKey}: ${String(cleanupErr)}`,
+          );
+        }
+
+        return finalizeWithFollowup({
+          text: "⚠️ Session history was corrupted. I've reset the conversation - please try again!",
+        });
+      }
+
       defaultRuntime.error(`Embedded agent failed before reply: ${message}`);
       return finalizeWithFollowup({
         text: isContextOverflow