diff --git a/extensions/anthropic/cli-backend.ts b/extensions/anthropic/cli-backend.ts
index 6141ac99df2..d62c84e3e61 100644
--- a/extensions/anthropic/cli-backend.ts
+++ b/extensions/anthropic/cli-backend.ts
@@ -63,6 +63,7 @@ export function buildAnthropicCliBackend(): CliBackendPlugin {
       imagePathScope: "workspace",
       sessionArg: "--session-id",
       sessionMode: "always",
+      reseedFromRawTranscriptWhenUncompacted: true,
       sessionIdFields: [...CLAUDE_CLI_SESSION_ID_FIELDS],
       systemPromptFileArg: "--append-system-prompt-file",
       systemPromptMode: "append",
diff --git a/extensions/anthropic/cli-shared.test.ts b/extensions/anthropic/cli-shared.test.ts
index 27d5f2589bd..7f4cf8455f9 100644
--- a/extensions/anthropic/cli-shared.test.ts
+++ b/extensions/anthropic/cli-shared.test.ts
@@ -261,6 +261,15 @@ describe("normalizeClaudeBackendConfig", () => {
     expect(backend.resolveExecutionArgs).toBe(resolveClaudeCliExecutionArgs);
   });
 
+  it("opts bundled Claude CLI into bounded raw transcript reseed without disabling native resume", () => {
+    const backend = buildAnthropicCliBackend();
+
+    expect(backend.config.reseedFromRawTranscriptWhenUncompacted).toBe(true);
+    expect(backend.config.sessionMode).toBe("always");
+    expect(backend.config.resumeArgs).toContain("--resume");
+    expect(backend.config.resumeArgs).toContain("{sessionId}");
+  });
+
   it("leaves claude cli subscription-managed, restricts setting sources, and clears inherited env overrides", () => {
     const backend = buildAnthropicCliBackend();