diff --git a/src/agents/cli-runner.reliability.test.ts b/src/agents/cli-runner.reliability.test.ts
index 56d3fd725d2..ec71f60e14a 100644
--- a/src/agents/cli-runner.reliability.test.ts
+++ b/src/agents/cli-runner.reliability.test.ts
@@ -74,6 +74,7 @@ function buildPreparedContext(params?: {
   sessionKey?: string;
   cliSessionId?: string;
   runId?: string;
+  openClawHistoryPrompt?: string;
 }): PreparedCliRunContext {
   const backend = {
     command: "codex",
@@ -115,6 +116,9 @@ function buildPreparedContext(params?: {
     systemPrompt: "You are a helpful assistant.",
     systemPromptReport: {} as PreparedCliRunContext["systemPromptReport"],
     bootstrapPromptWarningLines: [],
+    ...(params?.openClawHistoryPrompt
+      ? { openClawHistoryPrompt: params.openClawHistoryPrompt }
+      : {}),
     authEpochVersion: 2,
   };
 }
@@ -324,6 +328,56 @@ describe("runCliAgent reliability", () => {
     });
   });
 
+  it("seeds fresh CLI sessions from the OpenClaw transcript", async () => {
+    supervisorSpawnMock.mockResolvedValueOnce(
+      createManagedRun({
+        reason: "exit",
+        exitCode: 0,
+        exitSignal: null,
+        durationMs: 50,
+        stdout: "hello from cli",
+        stderr: "",
+        timedOut: false,
+        noOutputTimedOut: false,
+      }),
+    );
+
+    const result = await runPreparedCliAgent(
+      buildPreparedContext({
+        openClawHistoryPrompt:
+          "Continue this conversation using the OpenClaw transcript below.\n\nUser: earlier ask\n\nAssistant: earlier answer\n\n<next_user_message>\nhi\n</next_user_message>",
+      }),
+    );
+
+    expect(result.meta.finalPromptText).toContain("User: earlier ask");
+    expect(result.meta.finalPromptText).toContain("Assistant: earlier answer");
+  });
+
+  it("keeps resumed CLI sessions on native resume history", async () => {
+    supervisorSpawnMock.mockResolvedValueOnce(
+      createManagedRun({
+        reason: "exit",
+        exitCode: 0,
+        exitSignal: null,
+        durationMs: 50,
+        stdout: "hello from cli",
+        stderr: "",
+        timedOut: false,
+        noOutputTimedOut: false,
+      }),
+    );
+
+    const result = await runPreparedCliAgent(
+      buildPreparedContext({
+        cliSessionId: "cli-session",
+        openClawHistoryPrompt: "User: earlier ask",
+      }),
+    );
+
+    expect(result.meta.finalPromptText).not.toContain("User: earlier ask");
+    expect(result.meta.finalPromptText).toContain("hi");
+  });
+
   it("reports CLI reply backends as streaming until the managed run finishes", async () => {
     const operation = createReplyOperation({
       sessionKey: "agent:main:main",
diff --git a/src/agents/cli-runner/session-history.test.ts b/src/agents/cli-runner/session-history.test.ts
index b26949730c4..32bbff89d19 100644
--- a/src/agents/cli-runner/session-history.test.ts
+++ b/src/agents/cli-runner/session-history.test.ts
@@ -4,6 +4,7 @@ import path from "node:path";
 import { CURRENT_SESSION_VERSION } from "@mariozechner/pi-coding-agent";
 import { afterEach, describe, expect, it, vi } from "vitest";
 import {
+  buildCliSessionHistoryPrompt,
   loadCliSessionHistoryMessages,
   MAX_CLI_SESSION_HISTORY_FILE_BYTES,
   MAX_CLI_SESSION_HISTORY_MESSAGES,
@@ -218,3 +219,28 @@ describe("loadCliSessionHistoryMessages", () => {
     }
   });
 });
+
+describe("buildCliSessionHistoryPrompt", () => {
+  it("renders OpenClaw transcript history around the next user message", () => {
+    const prompt = buildCliSessionHistoryPrompt({
+      messages: [
+        { role: "user", content: "old ask" },
+        { role: "assistant", content: [{ type: "text", text: "old answer" }] },
+      ],
+      prompt: "new ask",
+    });
+
+    expect(prompt).toContain("User: old ask");
+    expect(prompt).toContain("Assistant: old answer");
+    expect(prompt).toContain("<next_user_message>\nnew ask\n</next_user_message>");
+  });
+
+  it("skips reseed text when the transcript has no renderable conversation", () => {
+    expect(
+      buildCliSessionHistoryPrompt({
+        messages: [{ role: "tool", content: "ignored" }],
+        prompt: "new ask",
+      }),
+    ).toBeUndefined();
+  });
+});
diff --git a/src/agents/command/cli-compaction.test.ts b/src/agents/command/cli-compaction.test.ts
new file mode 100644
index 00000000000..c83c5f64f1b
--- /dev/null
+++ b/src/agents/command/cli-compaction.test.ts
@@ -0,0 +1,170 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+import { CURRENT_SESSION_VERSION } from "@mariozechner/pi-coding-agent";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import type { SessionEntry } from "../../config/sessions/types.js";
+import type { OpenClawConfig } from "../../config/types.openclaw.js";
+import type { ContextEngine } from "../../context-engine/types.js";
+import {
+  resetCliCompactionTestDeps,
+  runCliTurnCompactionLifecycle,
+  setCliCompactionTestDeps,
+} from "./cli-compaction.js";
+
+function buildContextEngine(params: {
+  compactCalls: Array<Parameters<ContextEngine["compact"]>[0]>;
+}): ContextEngine {
+  return {
+    info: {
+      id: "legacy",
+      name: "Legacy Context Engine",
+    },
+    async ingest() {
+      return { ingested: false };
+    },
+    async assemble(assembleParams) {
+      return { messages: assembleParams.messages, estimatedTokens: 0 };
+    },
+    async compact(compactParams) {
+      params.compactCalls.push(compactParams);
+      return {
+        ok: true,
+        compacted: true,
+        result: {
+          summary: "compacted",
+          tokensBefore: compactParams.currentTokenCount ?? 0,
+          tokensAfter: 100,
+        },
+      };
+    },
+  };
+}
+
+async function writeSessionFile(params: { sessionFile: string; sessionId: string }) {
+  await fs.mkdir(path.dirname(params.sessionFile), { recursive: true });
+  await fs.writeFile(
+    params.sessionFile,
+    [
+      JSON.stringify({
+        type: "session",
+        version: CURRENT_SESSION_VERSION,
+        id: params.sessionId,
+        timestamp: new Date(0).toISOString(),
+        cwd: path.dirname(params.sessionFile),
+      }),
+      JSON.stringify({
+        type: "message",
+        message: { role: "user", content: "old ask", timestamp: 1 },
+      }),
+      JSON.stringify({
+        type: "message",
+        message: {
+          role: "assistant",
+          content: [{ type: "text", text: "old answer" }],
+          timestamp: 2,
+        },
+      }),
+      "",
+    ].join("\n"),
+    "utf-8",
+  );
+}
+
+describe("runCliTurnCompactionLifecycle", () => {
+  let tmpDir: string;
+
+  beforeEach(async () => {
+    tmpDir = await fs.mkdtemp(path.join(os.tmpdir(), "openclaw-cli-compaction-"));
+  });
+
+  afterEach(async () => {
+    resetCliCompactionTestDeps();
+    await fs.rm(tmpDir, { recursive: true, force: true });
+  });
+
+  it("compacts over-budget CLI transcripts and clears external CLI resume state", async () => {
+    const sessionKey = "agent:main:cli";
+    const sessionId = "session-cli";
+    const sessionFile = path.join(tmpDir, "session.jsonl");
+    const storePath = path.join(tmpDir, "sessions.json");
+    await writeSessionFile({ sessionFile, sessionId });
+
+    const sessionEntry: SessionEntry = {
+      sessionId,
+      updatedAt: Date.now(),
+      sessionFile,
+      contextTokens: 1_000,
+      totalTokens: 950,
+      totalTokensFresh: true,
+      cliSessionBindings: {
+        "claude-cli": { sessionId: "claude-session" },
+      },
+      cliSessionIds: {
+        "claude-cli": "claude-session",
+      },
+      claudeCliSessionId: "claude-session",
+    };
+    const sessionStore: Record<string, SessionEntry> = { [sessionKey]: sessionEntry };
+    await fs.writeFile(storePath, JSON.stringify(sessionStore, null, 2), "utf-8");
+
+    const compactCalls: Array<Parameters<ContextEngine["compact"]>[0]> = [];
+    const maintenance = vi.fn(async () => ({ changed: false, bytesFreed: 0, rewrittenEntries: 0 }));
+    setCliCompactionTestDeps({
+      resolveContextEngine: async () => buildContextEngine({ compactCalls }),
+      createPreparedEmbeddedPiSettingsManager: async () => ({
+        getCompactionReserveTokens: () => 200,
+        getCompactionKeepRecentTokens: () => 0,
+        applyOverrides: () => {},
+      }),
+      shouldPreemptivelyCompactBeforePrompt: () => ({
+        route: "fits",
+        shouldCompact: false,
+        estimatedPromptTokens: 600,
+        promptBudgetBeforeReserve: 800,
+        overflowTokens: 0,
+        toolResultReducibleChars: 0,
+        effectiveReserveTokens: 200,
+      }),
+      resolveLiveToolResultMaxChars: () => 20_000,
+      runContextEngineMaintenance: maintenance,
+    });
+
+    const updatedEntry = await runCliTurnCompactionLifecycle({
+      cfg: {} as OpenClawConfig,
+      sessionId,
+      sessionKey,
+      sessionEntry,
+      sessionStore,
+      storePath,
+      sessionAgentId: "main",
+      workspaceDir: tmpDir,
+      agentDir: tmpDir,
+      provider: "claude-cli",
+      model: "opus",
+    });
+
+    expect(compactCalls).toHaveLength(1);
+    expect(compactCalls[0]).toMatchObject({
+      sessionId,
+      sessionKey,
+      sessionFile,
+      tokenBudget: 1_000,
+      currentTokenCount: 950,
+      force: true,
+      compactionTarget: "budget",
+    });
+    expect(maintenance).toHaveBeenCalledWith(
+      expect.objectContaining({
+        reason: "compaction",
+        sessionId,
+        sessionKey,
+        sessionFile,
+      }),
+    );
+    expect(updatedEntry?.compactionCount).toBe(1);
+    expect(updatedEntry?.cliSessionBindings?.["claude-cli"]).toBeUndefined();
+    expect(updatedEntry?.cliSessionIds?.["claude-cli"]).toBeUndefined();
+    expect(updatedEntry?.claudeCliSessionId).toBeUndefined();
+  });
+});