diff --git a/.changeset/dedupe-reminder-survives-truncation.md b/.changeset/dedupe-reminder-survives-truncation.md
new file mode 100644
index 0000000000..d9e631623b
--- /dev/null
+++ b/.changeset/dedupe-reminder-survives-truncation.md
@@ -0,0 +1,5 @@
+---
+"@moonshot-ai/kimi-code": patch
+---
+
+Fix repeat-tool-call reminders never reaching the model for oversized tool results. The dedupe reminder was appended at the end of the tool output, but the >50K offload path keeps only a 2K head preview, so the reminder was silently cut off exactly in the large-output scenarios where repeat loops are most likely. Reminders are now prepended to the result output so they survive truncation. Covers both the v1 (`agent-core`) and v2 (`agent-core-v2`) engines.
diff --git a/packages/agent-core-v2/src/agent/toolDedupe/toolDedupeService.ts b/packages/agent-core-v2/src/agent/toolDedupe/toolDedupeService.ts
index bb84242936..b195809abe 100644
--- a/packages/agent-core-v2/src/agent/toolDedupe/toolDedupeService.ts
+++ b/packages/agent-core-v2/src/agent/toolDedupe/toolDedupeService.ts
@@ -80,18 +80,19 @@ interface CheckedToolCall {
   readonly syntheticResult: ToolDedupeResult | null;
 }
 
-function appendReminder(result: ToolDedupeResult, reminderText: string): ToolDedupeResult {
+// Prepend, not append: oversized results are later replaced by a head-only preview that would silently drop a tail reminder.
+function prependReminder(result: ToolDedupeResult, reminderText: string): ToolDedupeResult {
   const output = result.output;
   let newOutput: string | ContentPart[];
   if (typeof output === 'string') {
-    newOutput = output + reminderText;
+    newOutput = reminderText + output;
   } else {
-    const arr: ContentPart[] = [...output];
-    const last = arr.at(-1);
-    if (last !== undefined && last.type === 'text') {
-      arr[arr.length - 1] = { type: 'text', text: last.text + reminderText };
+    const arr = [...output];
+    const first = arr[0];
+    if (first !== undefined && first.type === 'text') {
+      arr[0] = { type: 'text', text: reminderText + first.text };
     } else {
-      arr.push({ type: 'text', text: reminderText });
+      arr.unshift({ type: 'text', text: reminderText });
     }
     newOutput = arr;
   }
@@ -101,7 +102,7 @@ function appendReminder(result: ToolDedupeResult, reminderText: string): ToolDed
 }
 
 function forceStopResult(result: ToolDedupeResult, reminderText: string): ToolDedupeResult {
-  const withReminder = appendReminder(result, reminderText);
+  const withReminder = prependReminder(result, reminderText);
   return { ...withReminder, stopTurn: true };
 }
 
@@ -277,13 +278,13 @@ export class AgentToolDedupeService extends Disposable implements IAgentToolDedu
       finalResult = forceStopResult(result, REMINDER_TEXT_3);
       action = 'stop';
     } else if (streak >= REPEAT_REMINDER_3_START) {
-      finalResult = appendReminder(result, REMINDER_TEXT_3);
+      finalResult = prependReminder(result, REMINDER_TEXT_3);
       action = 'r3';
     } else if (streak >= REPEAT_REMINDER_2_START) {
-      finalResult = appendReminder(result, makeReminderText2(streak));
+      finalResult = prependReminder(result, makeReminderText2(streak));
       action = 'r2';
     } else if (streak >= REPEAT_REMINDER_1_START) {
-      finalResult = appendReminder(result, REMINDER_TEXT_1);
+      finalResult = prependReminder(result, REMINDER_TEXT_1);
       action = 'r1';
     }
 
diff --git a/packages/agent-core-v2/test/agent/toolDedupe/toolDedupe.test.ts b/packages/agent-core-v2/test/agent/toolDedupe/toolDedupe.test.ts
index aa6dd80bd5..91277ae337 100644
--- a/packages/agent-core-v2/test/agent/toolDedupe/toolDedupe.test.ts
+++ b/packages/agent-core-v2/test/agent/toolDedupe/toolDedupe.test.ts
@@ -13,11 +13,15 @@ import { IAgentLoopService } from '#/agent/loop/loop';
 import type { ExecutableTool, ExecutableToolContext, ExecutableToolResult, ToolExecution, ToolResult } from '#/tool/toolContract';
 import type { ToolDidExecuteContext, ResolvedToolExecutionHookContext, BeforeExecuteDecision } from '#/agent/toolExecutor/toolHooks';
 import { IAgentToolDedupeService, type ToolDedupeResult } from '#/agent/toolDedupe/toolDedupe';
+import { IAgentToolResultTruncationService } from '#/agent/toolResultTruncation/toolResultTruncation';
+import { ToolResultTruncationService } from '#/agent/toolResultTruncation/toolResultTruncationService';
 import { AgentToolDedupeService, __testing as toolDedupeTesting } from '#/agent/toolDedupe/toolDedupeService';
 import { IAgentToolExecutorService, type ToolExecutionResult } from '#/agent/toolExecutor/toolExecutor';
 import { AgentToolExecutorService } from '#/agent/toolExecutor/toolExecutorService';
 import { IAgentToolRegistryService } from '#/agent/toolRegistry/toolRegistry';
 import { AgentToolRegistryService } from '#/agent/toolRegistry/toolRegistryService';
+import { InMemoryStorageService } from '#/persistence/backends/memory/inMemoryStorageService';
+import { IFileSystemStorageService } from '#/persistence/interface/storage';
 import { registerLogServices } from '../../_base/log/stubs';
 import { recordingTelemetry, type TelemetryRecord } from '../../app/telemetry/stubs';
 import { stubLoopWithHooks } from '../loop/stubs';
@@ -56,7 +60,7 @@ interface Harness {
 
 function createHarness(
   telemetry: ITelemetryService = recordingTelemetry(telemetryEvents),
-  options: { readonly executorEvents?: boolean } = {},
+  options: { readonly executorEvents?: boolean; readonly truncation?: 'real' } = {},
 ): Harness {
   const loop = stubLoopWithHooks();
   const events = options.executorEvents === true ? stubToolExecutorEvents() : undefined;
@@ -91,7 +95,12 @@ function createHarness(
       } else {
         reg.defineInstance(IAgentToolExecutorService, events.executor);
       }
-      registerToolResultTruncationServices(reg);
+      if (options.truncation === 'real') {
+        reg.defineInstance(IFileSystemStorageService, new InMemoryStorageService());
+        reg.define(IAgentToolResultTruncationService, ToolResultTruncationService);
+      } else {
+        registerToolResultTruncationServices(reg);
+      }
       reg.define(IAgentToolDedupeService, AgentToolDedupeService);
       registerLogServices(reg);
     },
@@ -441,8 +450,54 @@ describe('AgentToolDedupeService', () => {
     });
   });
 
+  describe('reminder survives oversized-result truncation (regression)', () => {
+    it('keeps the reminder inside the first 2K chars of an oversized result', async () => {
+      const h = createHarness();
+      const tool = new EchoTool('Read', () => ({ output: 'x'.repeat(60_000) }));
+      h.registry.register(tool);
+      let last: ToolResult | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        const [result] = await runStep(h, 1, i + 1, [toolCall(`c${String(i)}`, 'Read', { p: 1 })]);
+        last = result!.result;
+      }
+      const headPreview = (last!.output as string).slice(0, 2_000);
+      expect(headPreview).toContain('<system-reminder>');
+      expect(headPreview).toContain('what new information you expect');
+    });
+
+    it('prepends the reminder ahead of the original output', async () => {
+      const h = createHarness();
+      h.registry.register(new EchoTool('Read'));
+      let last: ToolResult | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        const [result] = await runStep(h, 1, i + 1, [toolCall(`c${String(i)}`, 'Read', { p: 1 })]);
+        last = result!.result;
+      }
+      expect((last!.output as string).startsWith('\n\n<system-reminder>')).toBe(true);
+    });
+
+    it('keeps the reminder visible through the real ToolResultTruncationService (composition)', async () => {
+      const h = createHarness(undefined, { truncation: 'real' });
+      const tool = new EchoTool('Read', () => ({ output: 'x'.repeat(60_000) }));
+      h.registry.register(tool);
+      let last: ToolResult | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        const [result] = await runStep(h, 1, i + 1, [toolCall(`c${String(i)}`, 'Read', { p: 1 })]);
+        last = result!.result;
+      }
+      const truncation = h.ix.get(IAgentToolResultTruncationService);
+      const modelResult = await truncation.truncateForModel({
+        toolName: 'Read',
+        toolCallId: 'c2',
+        result: last!,
+      });
+      expect(modelResult.output as string).toContain('<system-reminder>');
+      expect((modelResult.output as string).indexOf('<system-reminder>')).toBeLessThan(2_000);
+    });
+  });
+
   describe('reminder injection into ContentPart[] outputs', () => {
-    it('appends reminder1 to a trailing text part at streak 3', async () => {
+    it('prepends reminder1 to the leading text part at streak 3', async () => {
       const h = createHarness();
       const tool = new EchoTool('X', () => ({ output: [{ type: 'text', text: 'hello' }] }));
       h.registry.register(tool);
@@ -450,10 +505,10 @@ describe('AgentToolDedupeService', () => {
         await runStep(h, 1, i + 1, [toolCall(`p${String(i)}`, 'X', {})]);
       }
       const [final] = await runStep(h, 1, 3, [toolCall('final', 'X', {})]);
-      expect(final!.result.output).toBe('hello' + REMINDER_TEXT_1);
+      expect(final!.result.output).toBe(REMINDER_TEXT_1 + 'hello');
     });
 
-    it('appends reminder2 to a trailing text part at streak 5', async () => {
+    it('prepends reminder2 to the leading text part at streak 5', async () => {
       const h = createHarness();
       const tool = new EchoTool('X', () => ({ output: [{ type: 'text', text: 'hello' }] }));
       h.registry.register(tool);
@@ -461,22 +516,28 @@ describe('AgentToolDedupeService', () => {
         await runStep(h, 1, i + 1, [toolCall(`p${String(i)}`, 'X', { a: 1 })]);
       }
       const [final] = await runStep(h, 1, 5, [toolCall('final', 'X', { a: 1 })]);
-      expect(final!.result.output).toBe('hello' + makeReminderText2(5));
+      expect(final!.result.output).toBe(makeReminderText2(5) + 'hello');
     });
 
-    it('pushes a new text part when trailing part is non-text', async () => {
-      const h = createHarness();
-      const tool = new EchoTool('X', () => ({
+    it('prepends a new text part when leading part is non-text', async () => {
+      const h = createHarness(undefined, { executorEvents: true });
+      // The executor pipeline prepends its own text part to non-text outputs,
+      // so drive the hooks directly to exercise the dedupe's unshift branch.
+      const imageOnly = (): ExecutableToolResult => ({
         output: [{ type: 'image_url', imageUrl: { url: 'data:foo' } }],
-      }));
-      h.registry.register(tool);
-      for (let i = 0; i < 2; i += 1) {
-        await runStep(h, 1, i + 1, [toolCall(`p${String(i)}`, 'X', {})]);
+      });
+      let final: ToolDidExecuteContext | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        await beforeStep(h, 1, i + 1);
+        const id = i === 2 ? 'final' : `p${String(i)}`;
+        await h.fireBefore(willCtx(id, 'X', {}));
+        final = didCtx(id, 'X', {}, imageOnly());
+        await h.executor.hooks.onDidExecuteTool.run(final);
+        await afterStep(h, 1, i + 1);
       }
-      const [final] = await runStep(h, 1, 3, [toolCall('final', 'X', {})]);
       const arr = final!.result.output as Array<{ type: string; text?: string }>;
       expect(arr.some((part) => part.type === 'image_url')).toBe(true);
-      expect(arr.at(-1)).toEqual({ type: 'text', text: REMINDER_TEXT_1 });
+      expect(arr[0]).toEqual({ type: 'text', text: REMINDER_TEXT_1 });
     });
 
     it('preserves isError flag when injecting reminder', async () => {
diff --git a/packages/agent-core/src/agent/turn/tool-dedup.ts b/packages/agent-core/src/agent/turn/tool-dedup.ts
index f57679c8f7..4098ee9ef6 100644
--- a/packages/agent-core/src/agent/turn/tool-dedup.ts
+++ b/packages/agent-core/src/agent/turn/tool-dedup.ts
@@ -54,18 +54,19 @@ function makeKey(toolName: string, args: unknown): string {
   return `${toolName} ${canonicalTelemetryArgs(args)}`;
 }
 
-function appendReminder(result: ExecutableToolResult, reminderText: string): ExecutableToolResult {
+// Prepend, not append: oversized results are later replaced by a head-only preview that would silently drop a tail reminder.
+function prependReminder(result: ExecutableToolResult, reminderText: string): ExecutableToolResult {
   const output = result.output;
   let newOutput: string | ContentPart[];
   if (typeof output === 'string') {
-    newOutput = output + reminderText;
+    newOutput = reminderText + output;
   } else {
-    const arr: ContentPart[] = [...output];
-    const last = arr.at(-1);
-    if (last !== undefined && last.type === 'text') {
-      arr[arr.length - 1] = { type: 'text', text: last.text + reminderText };
+    const arr = [...output];
+    const first = arr[0];
+    if (first !== undefined && first.type === 'text') {
+      arr[0] = { type: 'text', text: reminderText + first.text };
     } else {
-      arr.push({ type: 'text', text: reminderText });
+      arr.unshift({ type: 'text', text: reminderText });
     }
     newOutput = arr;
   }
@@ -78,7 +79,7 @@ function forceStopResult(
   result: ExecutableToolResult,
   reminderText: string,
 ): ExecutableToolResult {
-  const withReminder = appendReminder(result, reminderText);
+  const withReminder = prependReminder(result, reminderText);
   return { ...withReminder, stopTurn: true };
 }
 
@@ -100,7 +101,7 @@ const DEDUP_PLACEHOLDER_RESULT: ExecutableToolResult = { output: '' };
  * - Same-step dedup: a duplicate `(toolName, args)` issued in the same LLM step
  *   reuses the original call's result instead of executing the tool twice.
  * - Cross-step dedup: when the exact same call is repeated consecutively
- *   across steps, the result returned to the model is suffixed with a system
+ *   across steps, the result returned to the model is prefixed with a system
  *   reminder once the streak hits 3. The reminder escalates as the streak
  *   grows: r1 (expectation-setting nudge) from streak 3, r2 (forced decision
  *   menu) from streak 5, r3 (final hand-off instruction) from streak 8. From streak 12
@@ -193,7 +194,7 @@ export class ToolCallDeduplicator {
   /**
    * Called from `finalizeToolResult`, in provider order. For first-occurrence
    * calls, projects the consecutive streak ending at this call and, if the
-   * threshold is reached, appends the system reminder, then resolves the
+   * threshold is reached, prepends the system reminder, then resolves the
    * deferred so subsequent same-step dups can fetch the real result. For
    * synthetic duplicates, awaits the original's deferred and returns its
    * value, discarding the placeholder.
@@ -237,13 +238,13 @@ export class ToolCallDeduplicator {
       finalResult = forceStopResult(result, REMINDER_TEXT_3);
       action = 'stop';
     } else if (streak >= REPEAT_REMINDER_3_START) {
-      finalResult = appendReminder(result, REMINDER_TEXT_3);
+      finalResult = prependReminder(result, REMINDER_TEXT_3);
       action = 'r3';
     } else if (streak >= REPEAT_REMINDER_2_START) {
-      finalResult = appendReminder(result, makeReminderText2(streak));
+      finalResult = prependReminder(result, makeReminderText2(streak));
       action = 'r2';
     } else if (streak >= REPEAT_REMINDER_1_START) {
-      finalResult = appendReminder(result, REMINDER_TEXT_1);
+      finalResult = prependReminder(result, REMINDER_TEXT_1);
       action = 'r1';
     }
 
diff --git a/packages/agent-core/test/agent/turn/tool-dedup.test.ts b/packages/agent-core/test/agent/turn/tool-dedup.test.ts
index f2aa09f9aa..ac4470d7b5 100644
--- a/packages/agent-core/test/agent/turn/tool-dedup.test.ts
+++ b/packages/agent-core/test/agent/turn/tool-dedup.test.ts
@@ -1,11 +1,16 @@
 import { describe, expect, it } from 'vitest';
 
+import { mkdtemp } from 'node:fs/promises';
+import { tmpdir } from 'node:os';
+import { join } from 'node:path';
+
 import type { ExecutableToolResult } from '../../../src/loop/types';
 import type {
   TelemetryClient,
   TelemetryProperties,
 } from '../../../src/telemetry';
 import { ToolCallDeduplicator, __testing } from '../../../src/agent/turn/tool-dedup';
+import { budgetToolResultForModel } from '../../../src/agent/turn/tool-result-budget';
 
 const { REMINDER_TEXT_1, REMINDER_TEXT_3, makeReminderText2 } = __testing;
 
@@ -235,8 +240,57 @@ describe('ToolCallDeduplicator', () => {
     });
   });
 
+  describe('reminder survives oversized-result truncation (regression)', () => {
+    it('keeps the reminder inside the first 2K chars of an oversized result', async () => {
+      const dedup = new ToolCallDeduplicator();
+      const big = 'x'.repeat(60_000);
+      let last: ExecutableToolResult | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        dedup.beginStep();
+        last = await runOriginal(dedup, `c${String(i)}`, 'Read', { p: 1 }, okResult(big));
+        dedup.endStep();
+      }
+      const headPreview = (last!.output as string).slice(0, 2_000);
+      expect(headPreview).toContain('<system-reminder>');
+      expect(headPreview).toContain('what new information you expect');
+    });
+
+    it('prepends the reminder ahead of the original output', async () => {
+      const dedup = new ToolCallDeduplicator();
+      let last: ExecutableToolResult | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        dedup.beginStep();
+        last = await runOriginal(dedup, `c${String(i)}`, 'Read', { p: 1 }, okResult('R'));
+        dedup.endStep();
+      }
+      expect((last!.output as string).startsWith('\n\n<system-reminder>')).toBe(true);
+      expect((last!.output as string).endsWith('R')).toBe(true);
+    });
+
+    it('keeps the reminder visible through the real budgetToolResultForModel offload (composition)', async () => {
+      const dedup = new ToolCallDeduplicator();
+      const big = 'x'.repeat(60_000);
+      let last: ExecutableToolResult | undefined;
+      for (let i = 0; i < 3; i += 1) {
+        dedup.beginStep();
+        last = await runOriginal(dedup, `c${String(i)}`, 'Read', { p: 1 }, okResult(big));
+        dedup.endStep();
+      }
+      const homedir = await mkdtemp(join(tmpdir(), 'dedupe-budget-'));
+      const modelResult = await budgetToolResultForModel({
+        homedir,
+        toolName: 'Read',
+        toolCallId: 'c2',
+        result: last!,
+      });
+      expect(typeof modelResult.output).toBe('string');
+      expect(modelResult.output as string).toContain('<system-reminder>');
+      expect((modelResult.output as string).indexOf('<system-reminder>')).toBeLessThan(2_000);
+    });
+  });
+
   describe('reminder injection into ContentPart[] outputs', () => {
-    it('appends reminder1 to a trailing text part at streak 3', async () => {
+    it('prepends reminder1 to the leading text part at streak 3', async () => {
       const dedup = new ToolCallDeduplicator();
       const arrayResult: ExecutableToolResult = {
         output: [{ type: 'text', text: 'hello' }],
@@ -253,10 +307,10 @@ describe('ToolCallDeduplicator', () => {
       const arr = final.output as Array<{ type: string; text: string }>;
       expect(arr).toHaveLength(1);
       expect(arr[0]!.type).toBe('text');
-      expect(arr[0]!.text).toBe('hello' + REMINDER_TEXT_1);
+      expect(arr[0]!.text).toBe(REMINDER_TEXT_1 + 'hello');
     });
 
-    it('appends reminder2 to a trailing text part at streak 5', async () => {
+    it('prepends reminder2 to the leading text part at streak 5', async () => {
       const dedup = new ToolCallDeduplicator();
       const arrayResult: ExecutableToolResult = {
         output: [{ type: 'text', text: 'hello' }],
@@ -273,10 +327,10 @@ describe('ToolCallDeduplicator', () => {
       const arr = final.output as Array<{ type: string; text: string }>;
       expect(arr).toHaveLength(1);
       expect(arr[0]!.type).toBe('text');
-      expect(arr[0]!.text).toBe('hello' + makeReminderText2(5));
+      expect(arr[0]!.text).toBe(makeReminderText2(5) + 'hello');
     });
 
-    it('pushes a new text part when trailing part is non-text', async () => {
+    it('prepends a new text part when leading part is non-text', async () => {
       const dedup = new ToolCallDeduplicator();
       const arrayResult: ExecutableToolResult = {
         output: [{ type: 'image_url', imageUrl: { url: 'data:foo' } }],
@@ -292,9 +346,9 @@ describe('ToolCallDeduplicator', () => {
       dedup.endStep();
       const arr = final.output as Array<{ type: string; text?: string }>;
       expect(arr).toHaveLength(2);
-      expect(arr[0]!.type).toBe('image_url');
-      expect(arr[1]!.type).toBe('text');
-      expect(arr[1]!.text).toBe(REMINDER_TEXT_1);
+      expect(arr[0]!.type).toBe('text');
+      expect(arr[0]!.text).toBe(REMINDER_TEXT_1);
+      expect(arr[1]!.type).toBe('image_url');
     });
 
     it('preserves isError flag when injecting reminder', async () => {