diff --git a/src/config/sessions/session-accessor.conformance.test.ts b/src/config/sessions/session-accessor.conformance.test.ts
index 36d303641025..a226bc533f69 100644
--- a/src/config/sessions/session-accessor.conformance.test.ts
+++ b/src/config/sessions/session-accessor.conformance.test.ts
@@ -1660,6 +1660,77 @@ describe("sqlite session normalization", () => {
     ).toEqual(["agent:main:newer", "agent:main:newest"]);
   });
 
+  it("preserves pinned SQLite entries and transcripts during write-triggered capping", async () => {
+    vi.mocked(getRuntimeConfig).mockReturnValue({
+      session: {
+        maintenance: {
+          mode: "enforce",
+          pruneAfter: "365d",
+          maxEntries: 2,
+        },
+      },
+    });
+    const env = { ...process.env, OPENCLAW_STATE_DIR: paths.stateDir };
+    const scopeFor = (sessionKey: string) => ({
+      agentId: "main",
+      env,
+      sessionKey,
+      storePath: paths.sqlitePath,
+    });
+    const pinnedKey = "agent:main:pinned-dashboard";
+    const pinnedSessionId = "pinned-dashboard-session";
+    const pinnedTranscriptEvent = {
+      id: "pinned-event",
+      timestamp: new Date().toISOString(),
+      type: "metadata",
+    };
+
+    await patchSessionEntryCore(
+      scopeFor(pinnedKey),
+      () => ({ sessionId: pinnedSessionId, updatedAt: 1, pinnedAt: 2 }),
+      {
+        fallbackEntry: { sessionId: pinnedSessionId, updatedAt: 1, pinnedAt: 2 },
+        replaceEntry: true,
+        skipMaintenance: true,
+      },
+    );
+    await appendTranscriptEvent(
+      { ...scopeFor(pinnedKey), sessionId: pinnedSessionId },
+      pinnedTranscriptEvent,
+    );
+    await patchSessionEntryCore(
+      scopeFor("agent:main:recent-dashboard"),
+      () => ({ sessionId: "recent-dashboard-session", updatedAt: 3 }),
+      {
+        fallbackEntry: { sessionId: "recent-dashboard-session", updatedAt: 3 },
+        replaceEntry: true,
+        skipMaintenance: true,
+      },
+    );
+
+    await patchSessionEntryCore(
+      scopeFor("agent:main:maintenance-trigger"),
+      () => ({ sessionId: "maintenance-trigger-session", updatedAt: 4 }),
+      {
+        fallbackEntry: { sessionId: "maintenance-trigger-session", updatedAt: 4 },
+        replaceEntry: true,
+      },
+    );
+
+    expect(loadSessionEntry(scopeFor(pinnedKey))).toMatchObject({
+      pinnedAt: 2,
+      sessionId: pinnedSessionId,
+    });
+    await expect(
+      loadTranscriptEvents({
+        agentId: "main",
+        env,
+        sessionId: pinnedSessionId,
+        storePath: paths.sqlitePath,
+      }),
+    ).resolves.toEqual([pinnedTranscriptEvent]);
+  });
+
   it("preserves an admitted SQLite session when another session triggers maintenance", async () => {
     vi.mocked(getRuntimeConfig).mockReturnValue({
       session: {
diff --git a/src/config/sessions/store-maintenance.ts b/src/config/sessions/store-maintenance.ts
index ecabc57142d0..70dbd34cefae 100644
--- a/src/config/sessions/store-maintenance.ts
+++ b/src/config/sessions/store-maintenance.ts
@@ -428,8 +428,8 @@ export function shouldPreserveMaintenanceEntry(params: {
   entry: SessionEntry | undefined;
   preserveKeys?: ReadonlySet<string>;
 }): boolean {
-  // Archived sessions are user-shelved; only an explicit sessions.delete may remove them.
-  if (params.entry?.archivedAt !== undefined) {
+  // Archived and pinned sessions are user-retained; only an explicit user action may release them.
+  if (params.entry?.archivedAt !== undefined || params.entry?.pinnedAt !== undefined) {
     return true;
   }
   // A model lock is durable harness ownership, not merely a UI restriction.
diff --git a/src/config/sessions/store.pruning.test.ts b/src/config/sessions/store.pruning.test.ts
index a5ef6e11a16a..5ad86652ac26 100644
--- a/src/config/sessions/store.pruning.test.ts
+++ b/src/config/sessions/store.pruning.test.ts
@@ -142,6 +142,20 @@ describe("pruneStaleEntries", () => {
     expect(pruneStaleEntries(store, 30 * DAY_MS)).toBe(1);
     expect(store.archived).toBeUndefined();
   });
+
+  it("preserves pinned entries until they are unpinned", () => {
+    const now = Date.now();
+    const store = makeStore([
+      ["pinned", { ...makeEntry(now - 31 * DAY_MS), pinnedAt: now - DAY_MS }],
+    ]);
+
+    expect(pruneStaleEntries(store, 30 * DAY_MS)).toBe(0);
+    expect(store).toHaveProperty("pinned");
+
+    delete store.pinned?.pinnedAt;
+    expect(pruneStaleEntries(store, 30 * DAY_MS)).toBe(1);
+    expect(store.pinned).toBeUndefined();
+  });
 });
 
 describe("resolveQuotaSuspensionEntryMaintenance", () => {
@@ -710,6 +724,20 @@ describe("capEntryCount", () => {
     expect(store.old).toBeUndefined();
   });
 
+  it("preserves pinned sessions when capping", () => {
+    const now = Date.now();
+    const store = makeStore([
+      ["pinned", { ...makeEntry(now - 10 * DAY_MS), pinnedAt: now - 5 * DAY_MS }],
+      ["recent", makeEntry(now)],
+      ["old", makeEntry(now - DAY_MS)],
+    ]);
+
+    expect(capEntryCount(store, 2)).toBe(1);
+    expect(store).toHaveProperty("pinned");
+    expect(store).toHaveProperty("recent");
+    expect(store.old).toBeUndefined();
+  });
+
   it("preserves runtime-provided pending subagent sessions when capping", () => {
     const now = Date.now();
     const childKey = "agent:main:subagent:child";