diff --git a/apps/web/src/components/ChatView.logic.test.ts b/apps/web/src/components/ChatView.logic.test.ts
index 7de02cc3941ad..520658182b267 100644
--- a/apps/web/src/components/ChatView.logic.test.ts
+++ b/apps/web/src/components/ChatView.logic.test.ts
@@ -1094,16 +1094,21 @@ describe("planComposerTurn", () => {
     });
   });
 
-  it("queues behind a compaction of a stale session, except for /compact itself", () => {
+  it("queues behind a compaction of a stale session, except for /compact and /clear", () => {
     const stale = { ...base, resumeCompactionTokens: 120_000 };
-    for (const messageText of ["hello", "/compactfoo"]) {
+    for (const messageText of ["hello", "/compactfoo", "/clearly not a command"]) {
       expect(planComposerTurn({ ...stale, messageText })).toMatchObject({
         compactBeforeSend: true,
         turnDispatchMode: "queue",
         shouldQueueBehindActiveRun: true,
       });
     }
-    for (const messageText of ["/COMPACT", "/compact keep the API notes", "/compact\n  tests"]) {
+    for (const messageText of [
+      "/COMPACT",
+      "/compact keep the API notes",
+      "/compact\n  tests",
+      "/clear",
+    ]) {
       expect(planComposerTurn({ ...stale, messageText })).toMatchObject({
         compactBeforeSend: false,
         turnDispatchMode: "auto",
diff --git a/apps/web/src/components/ChatView.logic.ts b/apps/web/src/components/ChatView.logic.ts
index 09a25ee55910d..e108c7f2ce39a 100644
--- a/apps/web/src/components/ChatView.logic.ts
+++ b/apps/web/src/components/ChatView.logic.ts
@@ -4,7 +4,7 @@ import {
   deriveThreadRuntime,
 } from "@t3tools/client-runtime/state/thread-execution";
 import { checkpointFileTotals } from "@t3tools/client-runtime/state/thread-checkpoints";
-import { COMPACT_COMMAND_PATTERN } from "@t3tools/client-runtime/state/context-window";
+import { NO_COMPACT_BEFORE_COMMAND_PATTERN } from "@t3tools/client-runtime/state/context-window";
 import { derivePendingBackgroundWork } from "@t3tools/shared/orchestrationV2PendingBackgroundWork";
 import {
   latestUnheldRun,
@@ -1319,7 +1319,7 @@ export function planComposerTurn(input: {
     !input.freshContext &&
     input.resumeCompactionTokens !== null &&
     !input.keepFullHistory &&
-    !COMPACT_COMMAND_PATTERN.test(input.messageText);
+    !NO_COMPACT_BEFORE_COMMAND_PATTERN.test(input.messageText);
   const dispatchMode =
     input.freshContext && (input.dispatchMode === "steer" || input.dispatchMode === "restart")
       ? "queue"
diff --git a/packages/client-runtime/src/state/contextWindow.test.ts b/packages/client-runtime/src/state/contextWindow.test.ts
index 3f1a4d3d41994..3f7150b812b35 100644
--- a/packages/client-runtime/src/state/contextWindow.test.ts
+++ b/packages/client-runtime/src/state/contextWindow.test.ts
@@ -256,6 +256,7 @@ describe("shouldCompactBeforeSend", () => {
     { name: "while the thread is working", threadIdle: false, expected: false },
     { name: "with no conversation but /compact", onlyCompactMessages: true, expected: false },
     { name: "for a typed /compact", text: "/compact keep the plan", expected: false },
+    { name: "for a typed /clear", text: "/clear", expected: false },
   ] as const)("$name", ({ name: _name, expected, ...overrides }) => {
     expect(shouldCompactBeforeSend(sendInput(overrides as Parameters<typeof sendInput>[0]))).toBe(
       expected,
diff --git a/packages/client-runtime/src/state/contextWindow.ts b/packages/client-runtime/src/state/contextWindow.ts
index 66c48807465af..0701f91b1c59b 100644
--- a/packages/client-runtime/src/state/contextWindow.ts
+++ b/packages/client-runtime/src/state/contextWindow.ts
@@ -22,8 +22,9 @@ import type { ThreadStructure, ThreadStructureTurnItem } from "./models.ts";
 const CLAUDE_RESUME_COMPACTION_FALLBACK_MS = 70 * 60_000;
 
 // A typed `/compact`, with or without instructions, is already the compaction. Queueing a
-// bare one ahead of it would run an uninstructed compaction first and charge for two.
-export const COMPACT_COMMAND_PATTERN = /^\/compact(?:\s|$)/i;
+// bare one ahead of it would run an uninstructed compaction first and charge for two. A typed
+// `/clear` discards the old context, so compacting it first pays for a summary nobody reads.
+export const NO_COMPACT_BEFORE_COMMAND_PATTERN = /^\/(?:compact|clear)(?:\s|$)/i;
 
 function asFiniteNumber(value: unknown): number | null {
   return typeof value === "number" && Number.isFinite(value) ? value : null;
@@ -265,7 +266,7 @@ export function shouldCompactBeforeSend(input: {
   if (
     provider === undefined ||
     !input.threadIdle ||
-    COMPACT_COMMAND_PATTERN.test(input.text) ||
+    NO_COMPACT_BEFORE_COMMAND_PATTERN.test(input.text) ||
     resolveIdleCompaction(input.settings, provider.instanceId) === "off" ||
     !provider.slashCommands.some((command) => command.name === "compact") ||
     resolvePendingHandoff(projection, input.selection, input.providers) !== null ||