From 92c0b0789a7a5d32f79adc83f9bdd69f9fb3e4d2 Mon Sep 17 00:00:00 2001
From: Per <123196452+noxaur@users.noreply.github.com>
Date: Fri, 30 Oct 2026 21:47:23 +0100
Subject: [PATCH 1/7] fix(claude): context meter follows the /autocompact
 window

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 .../Adapters/ClaudeAdapterV2.test.ts          |  77 ++++++++++++-
 .../Adapters/ClaudeAdapterV2.ts               | 105 +++++++++++++-----
 apps/web/src/lib/contextWindow.test.ts        |   6 +-
 apps/web/src/lib/contextWindow.ts             |   6 +-
 4 files changed, 158 insertions(+), 36 deletions(-)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 40f33b3a1a30..b668aa108bba 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -738,7 +738,7 @@ describe("ClaudeAdapterV2 context usage", () => {
       },
       CLAUDE_TEST_MODEL_SELECTION,
       "2026-08-29T00:03:00.000Z",
-      "",
+      undefined,
       DateTime.makeUnsafe("2026-08-29T00:00:00.000Z"),
     );
     assert.strictEqual(usage.promptCacheExpiresAt, "2026-08-29T00:05:00.000Z");
@@ -770,7 +770,7 @@ describe("ClaudeAdapterV2 approval presentation", () => {
       permissionMode: "bypassPermissions",
       prompt: "Claude wants to run git push",
       callbackOptions: {
-        matchedAskRule: { source: "userSettings", toolName: "Bash", ruleContent: "git push:*" },
+        matchedAskRule: { source: "user", toolName: "Bash", ruleContent: "git push:*" },
       },
     });
     assert.deepEqual(presentation, { fullAccessOverride: "ask_rule" });
@@ -6086,18 +6086,79 @@ describe("ClaudeAdapterV2 background wake turns", () => {
     ),
   );
 
-  it.effect.each([
+  it.effect.each<{
+    autoCompactWindow: string;
+    model: string;
+    threshold: number | undefined;
+    userSettings?: string;
+    projectSettings?: string;
+    launchArgs?: string;
+  }>([
     { autoCompactWindow: "", model: "claude-sonnet-4-6", threshold: undefined },
     { autoCompactWindow: "150000", model: "claude-sonnet-4-6", threshold: 150_000 },
     { autoCompactWindow: "200000", model: "claude-sonnet-4-6", threshold: undefined },
     { autoCompactWindow: "650000", model: "claude-sonnet-4-6", threshold: undefined },
     { autoCompactWindow: "650000", model: "uncatalogued-model", threshold: 650_000 },
+    // /autocompact writes the per-model value, which beats the file's top-level one.
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      userSettings:
+        '{"autoCompactWindow":300000,"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+      threshold: 400_000,
+    },
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+      projectSettings: '{"autoCompactWindow":300000}',
+      threshold: 300_000,
+    },
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      userSettings: '{"autoCompactWindow":300000}',
+      projectSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":"auto"}}}',
+      threshold: undefined,
+    },
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+      launchArgs: `--settings '{"autoCompactWindow":250000}'`,
+      threshold: 250_000,
+    },
+    {
+      autoCompactWindow: "250000",
+      model: "claude-opus-5-5",
+      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+      threshold: 250_000,
+    },
   ])(
-    "ignores stale snapshots after compaction and reports threshold $autoCompactWindow for $model",
-    ({ autoCompactWindow, model, threshold }) =>
+    "ignores stale snapshots after compaction and reports threshold $threshold for $model",
+    ({
+      autoCompactWindow,
+      model,
+      threshold,
+      userSettings = "{}",
+      projectSettings,
+      launchArgs = "",
+    }) =>
       Effect.gen(function* () {
+        const fileSystem = yield* FileSystem.FileSystem;
+        const path = yield* Path.Path;
+        const home = yield* fileSystem.makeTempDirectoryScoped({ prefix: "t3-claude-compact-" });
+        const project = yield* fileSystem.makeTempDirectoryScoped({ prefix: "t3-claude-compact-" });
+        yield* fileSystem.writeFileString(path.join(home, "settings.json"), userSettings);
+        if (projectSettings !== undefined) {
+          yield* fileSystem.makeDirectory(path.join(project, ".claude"));
+          yield* fileSystem.writeFileString(
+            path.join(project, ".claude", "settings.json"),
+            projectSettings,
+          );
+        }
         const harness = yield* makeWakeHarnessWithOptions({
-          settings: { ...DEFAULT_CLAUDE_SETTINGS, autoCompactWindow },
+          settings: { ...DEFAULT_CLAUDE_SETTINGS, autoCompactWindow, homePath: home, launchArgs },
         });
         yield* harness.runtime.startTurn(
           makeClaudeTestTurnInput({
@@ -6108,6 +6169,10 @@ describe("ClaudeAdapterV2 background wake turns", () => {
             text: "Continue.",
             attachments: [],
             modelSelection: { ...CLAUDE_TEST_MODEL_SELECTION, model },
+            runtimePolicy: ProviderAdapter.ProviderAdapterV2RuntimePolicy.make({
+              ...CLAUDE_TEST_RUNTIME_POLICY,
+              cwd: project,
+            }),
           }),
         );
         const usage = { ...zeroUsage, input_tokens: 1_000, output_tokens: 75 };
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index f42f37d1ab1b..c0adcbbd7da2 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -231,10 +231,14 @@ function claudePromptCacheTtlMs(
 }
 
 // Claude caps the window at the model's context, so a setting at or above it never applies.
-function claudeAutoCompactThreshold(autoCompactWindow: string, maxTokens: number | null) {
-  const threshold = Number(autoCompactWindow);
-  return threshold > 0 && (maxTokens === null || threshold < maxTokens)
-    ? { autoCompactThreshold: threshold }
+function claudeAutoCompactThreshold(
+  autoCompactWindow: number | undefined,
+  maxTokens: number | null,
+) {
+  return autoCompactWindow !== undefined &&
+    autoCompactWindow > 0 &&
+    (maxTokens === null || autoCompactWindow < maxTokens)
+    ? { autoCompactThreshold: autoCompactWindow }
     : {};
 }
 
@@ -260,7 +264,7 @@ export function claudeProviderTurnTokenUsage(
   },
   modelSelection: ModelSelection,
   updatedAt: string,
-  autoCompactWindow = "",
+  autoCompactWindow?: number,
   requestedAt?: DateTime.Utc,
 ) {
   const inputTokens = claudeMessageInputTokens(usage);
@@ -2619,6 +2623,20 @@ const decodeClaudeSubagentCacheSettings = Schema.decodeUnknownEffect(
     ),
   ),
 );
+const ClaudeAutoCompactWindowSetting = Schema.Union([Schema.Finite, Schema.Literal("auto")]);
+const ClaudeAutoCompactSettings = Schema.Struct({
+  autoCompactWindow: Schema.optionalKey(ClaudeAutoCompactWindowSetting),
+  modelSettings: Schema.optionalKey(
+    Schema.Record(
+      Schema.String,
+      Schema.Struct({ autoCompactWindow: Schema.optionalKey(ClaudeAutoCompactWindowSetting) }),
+    ),
+  ),
+});
+const decodeClaudeAutoCompactSettings = Schema.decodeUnknownOption(ClaudeAutoCompactSettings);
+const decodeClaudeAutoCompactSettingsFile = Schema.decodeUnknownEffect(
+  fromLenientJson(ClaudeAutoCompactSettings),
+);
 const decodeClaudeEnvSettings = Schema.decodeUnknownEffect(
   fromLenientJson(
     Schema.StructWithRest(
@@ -3898,6 +3916,7 @@ interface ActiveClaudeTurnContext {
       { readonly startedAt: DateTime.Utc; readonly ordinal: number; text: string }
     >;
   };
+  readonly autoCompactWindow: number | undefined;
   // Snapshots repeat message_start input, sometimes as zeros, so only fill gaps in streamed usage.
   // Compaction clears usage without forgetting the root request.
   // `requestedAt` starts the request's prompt cache lifetime.
@@ -4509,25 +4528,26 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
       if (path.dirname(directory) === directory) return cwd;
     }
   });
-  // Settings env beats the process env, --settings over local over project over user, and a local
-  // file an older Claude Code left in cwd applies under the root one. resolveSettings reads local
-  // from cwd only.
+  // Local over project over user, and a local file an older Claude Code left in cwd applies under
+  // the root one. resolveSettings reads local from cwd only.
+  const settingsFilesByPrecedence = Effect.fn("ClaudeAdapterV2.settingsFilesByPrecedence")(
+    function* (cwd: string | null) {
+      if (cwd === null) return [path.join(homePath, "settings.json")];
+      const localDirectory = yield* localSettingsDirectory(cwd);
+      return [
+        path.join(localDirectory, ".claude", "settings.local.json"),
+        ...(localDirectory === cwd ? [] : [path.join(cwd, ".claude", "settings.local.json")]),
+        path.join(cwd, ".claude", "settings.json"),
+        path.join(homePath, "settings.json"),
+      ];
+    },
+  );
+  // Settings env beats the process env, and --settings beats every settings file.
   const resolveToolSearchOverride = Effect.fn("ClaudeAdapterV2.resolveToolSearchOverride")(
     function* (cwd: string | null, launchArgSettings: ClaudeSdkSettings | undefined) {
       const launchValue = launchArgSettings?.env?.ENABLE_TOOL_SEARCH;
       if (typeof launchValue === "string") return claudeToolSearchOverride(launchValue);
-      const localDirectory = cwd === null ? null : yield* localSettingsDirectory(cwd);
-      const settingsFiles = [
-        ...(cwd === null || localDirectory === null
-          ? []
-          : [
-              path.join(localDirectory, ".claude", "settings.local.json"),
-              ...(localDirectory === cwd ? [] : [path.join(cwd, ".claude", "settings.local.json")]),
-              path.join(cwd, ".claude", "settings.json"),
-            ]),
-        path.join(homePath, "settings.json"),
-      ];
-      for (const settingsFile of settingsFiles) {
+      for (const settingsFile of yield* settingsFilesByPrecedence(cwd)) {
         const value = yield* readToolSearchSetting(settingsFile);
         if (value !== undefined) return claudeToolSearchOverride(value);
       }
@@ -4535,6 +4555,39 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
     },
   );
 
+  // Claude Code's auto-compact window: its env var, then T3's setting (sent as flag settings), then
+  // --settings, then settings files. In one source, modelSettings.<model>.autoCompactWindow (what
+  // /autocompact writes) replaces the top-level value; "auto" keeps Claude's tuned window.
+  const resolveAutoCompactWindow = Effect.fn("ClaudeAdapterV2.resolveAutoCompactWindow")(function* (
+    cwd: string | null,
+    modelSelection: ModelSelection,
+  ) {
+    const fromEnvironment = Number(adapterOptions.environment.CLAUDE_CODE_AUTO_COMPACT_WINDOW);
+    if (fromEnvironment > 0) return fromEnvironment;
+    const fromT3 = Number(adapterOptions.settings.autoCompactWindow);
+    if (fromT3 > 0) return fromT3;
+    const model = compileClaudeModelSelection(modelSelection).apiModelId.replace(/\[1m\]$/i, "");
+    const windowIn = (settings: typeof ClaudeAutoCompactSettings.Type | undefined) =>
+      settings?.modelSettings?.[model]?.autoCompactWindow ?? settings?.autoCompactWindow;
+    const launchArgSettings = yield* readClaudeLaunchArgSettings({
+      settings: adapterOptions.settings,
+      cwd,
+      fileSystem,
+      path,
+    }).pipe(Effect.orElseSucceed(() => undefined));
+    let value = windowIn(Option.getOrUndefined(decodeClaudeAutoCompactSettings(launchArgSettings)));
+    for (const settingsFile of yield* settingsFilesByPrecedence(cwd)) {
+      if (value !== undefined) break;
+      value = windowIn(
+        yield* fileSystem.readFileString(settingsFile).pipe(
+          Effect.flatMap(decodeClaudeAutoCompactSettingsFile),
+          Effect.orElseSucceed(() => undefined),
+        ),
+      );
+    }
+    return value === "auto" ? undefined : value;
+  });
+
   const userInvocableSkills = (cwd: string | null) =>
     discoverClaudeSkills(
       adapterOptions.settings,
@@ -4916,7 +4969,7 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
             usage,
             context.input.modelSelection,
             DateTime.formatIso(now),
-            adapterOptions.settings.autoCompactWindow,
+            context.autoCompactWindow,
             context.streamUsage?.requestedAt,
           );
           if (tokenUsage.inputTokens <= 0) return;
@@ -8495,10 +8548,7 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
                   tokenUsage: {
                     usedTokens: afterTokenCount,
                     maxTokens,
-                    ...claudeAutoCompactThreshold(
-                      adapterOptions.settings.autoCompactWindow,
-                      maxTokens,
-                    ),
+                    ...claudeAutoCompactThreshold(context.autoCompactWindow, maxTokens),
                     updatedAt: DateTime.formatIso(now),
                   },
                 },
@@ -10172,8 +10222,13 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
                     Effect.provideService(Path.Path, path),
                   );
             const querySession = yield* openQuery(turnInput, nativeThreadId);
+            const autoCompactWindow = yield* resolveAutoCompactWindow(
+              turnInput.runtimePolicy.cwd,
+              turnInput.modelSelection,
+            );
             const context: ActiveClaudeTurnContext = {
               input: turnInput,
+              autoCompactWindow,
               queryPolicy: querySession.queryPolicy,
               nativeThreadId,
               nativeTurnId,
diff --git a/apps/web/src/lib/contextWindow.test.ts b/apps/web/src/lib/contextWindow.test.ts
index c27ddd9a0465..b9f52f208239 100644
--- a/apps/web/src/lib/contextWindow.test.ts
+++ b/apps/web/src/lib/contextWindow.test.ts
@@ -60,9 +60,9 @@ describe("live provider-turn usage (#8144)", () => {
     const snapshot = deriveLatestContextWindowSnapshot([], usage);
     expect(snapshot).not.toBeNull();
     expect(snapshot?.usedTokens).toBe(42_000);
-    expect(snapshot?.maxTokens).toBe(200_000);
-    expect(snapshot?.remainingTokens).toBe(158_000);
-    expect(snapshot?.usedPercentage).toBe(21);
+    expect(snapshot?.maxTokens).toBe(150_000);
+    expect(snapshot?.remainingTokens).toBe(108_000);
+    expect(snapshot?.usedPercentage).toBeCloseTo(28);
     expect(snapshot?.autoCompactThreshold).toBe(150_000);
     expect(
       formatContextWindowCompactionMessage("Claude Sonnet 4.6", snapshot?.autoCompactThreshold),
diff --git a/apps/web/src/lib/contextWindow.ts b/apps/web/src/lib/contextWindow.ts
index 8c449249e033..a04a434f9462 100644
--- a/apps/web/src/lib/contextWindow.ts
+++ b/apps/web/src/lib/contextWindow.ts
@@ -63,7 +63,8 @@ export function deriveLatestContextWindowSnapshot(
 ): ContextWindowSnapshot | null {
   if (liveUsage != null) {
     const usedTokens = Math.max(0, liveUsage.usedTokens);
-    const maxTokens = liveUsage.maxTokens ?? null;
+    // Like Claude's /context, measure against the auto-compact window when it is smaller.
+    const maxTokens = liveUsage.autoCompactThreshold ?? liveUsage.maxTokens ?? null;
     const usedPercentage =
       maxTokens !== null && maxTokens > 0 ? Math.min(100, (usedTokens / maxTokens) * 100) : null;
     const remainingTokens =
@@ -100,7 +101,8 @@ export function deriveLatestContextWindowSnapshot(
     providerUsage !== undefined &&
     providerUsageUpdatedAt !== undefined
   ) {
-    const maxTokens = asFiniteNumber(providerUsage.maxTokens);
+    const maxTokens =
+      asFiniteNumber(providerUsage.autoCompactThreshold) ?? asFiniteNumber(providerUsage.maxTokens);
     const usedTokens = providerUsage.usedTokens;
     const usedPercentage =
       maxTokens !== null && maxTokens > 0 ? Math.min(100, (usedTokens / maxTokens) * 100) : null;

From b792d6d7ad1dc6d1da12c3c3bb1524d46fc6e69f Mon Sep 17 00:00:00 2001
From: Per <123196452+noxaur@users.noreply.github.com>
Date: Fri, 30 Oct 2026 22:04:19 +0100
Subject: [PATCH 2/7] fix(claude): read --autocompact and Claude's window
 formats

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 .../Adapters/ClaudeAdapterV2.test.ts          | 38 ++++++++++++++++
 .../Adapters/ClaudeAdapterV2.ts               | 43 ++++++++++++++++---
 apps/web/src/lib/contextWindow.test.ts        |  4 +-
 3 files changed, 78 insertions(+), 7 deletions(-)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 5519c9ad5911..8608ffc5ca19 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -6360,6 +6360,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
     userSettings?: string;
     projectSettings?: string;
     launchArgs?: string;
+    environment?: NodeJS.ProcessEnv;
   }>([
     { autoCompactWindow: "", model: "claude-sonnet-4-6", threshold: undefined },
     { autoCompactWindow: "150000", model: "claude-sonnet-4-6", threshold: 150_000 },
@@ -6401,6 +6402,41 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
       threshold: 250_000,
     },
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      userSettings: '{"autoCompactWindow":150000.5}',
+      threshold: undefined,
+    },
+    // --autocompact reads 100 to 1000 as thousands and beats T3's setting and settings files.
+    {
+      autoCompactWindow: "300000",
+      model: "claude-opus-5-5",
+      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+      launchArgs: "--autocompact 250",
+      threshold: 250_000,
+    },
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+      launchArgs: "--autocompact auto",
+      threshold: undefined,
+    },
+    // The env var beats every other source, takes k/M suffixes, and clamps to 100k.
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      launchArgs: "--autocompact 250k",
+      environment: { CLAUDE_CODE_AUTO_COMPACT_WINDOW: "200k" },
+      threshold: 200_000,
+    },
+    {
+      autoCompactWindow: "",
+      model: "claude-opus-5-5",
+      environment: { CLAUDE_CODE_AUTO_COMPACT_WINDOW: "200" },
+      threshold: 100_000,
+    },
   ])(
     "ignores stale snapshots after compaction and reports threshold $threshold for $model",
     ({
@@ -6410,6 +6446,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       userSettings = "{}",
       projectSettings,
       launchArgs = "",
+      environment,
     }) =>
       Effect.gen(function* () {
         const fileSystem = yield* FileSystem.FileSystem;
@@ -6426,6 +6463,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
         }
         const harness = yield* makeWakeHarnessWithOptions({
           settings: { ...DEFAULT_CLAUDE_SETTINGS, autoCompactWindow, homePath: home, launchArgs },
+          ...(environment === undefined ? {} : { environment }),
         });
         yield* harness.runtime.startTurn(
           makeClaudeTestTurnInput({
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 3543dd6f6df8..2970265d5025 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -233,6 +233,28 @@ function claudePromptCacheTtlMs(
   return undefined;
 }
 
+// Claude reads a token count or a k/M suffix and clamps it to 100k-1M. Only --autocompact also
+// takes "auto" and reads 100 to 1000 as thousands.
+function parseClaudeAutoCompactWindow(raw: string | null | undefined, source: "env" | "flag") {
+  const value = raw?.trim().toLowerCase();
+  if (value === "auto") return source === "flag" ? "auto" : undefined;
+  const match = value === undefined ? null : /^(\d+(?:\.\d+)?)([km])?$/.exec(value);
+  if (match === null) return undefined;
+  const amount = Number(match[1]);
+  const scale =
+    match[2] === "k"
+      ? 1_000
+      : match[2] === "m"
+        ? 1_000_000
+        : source === "flag" && amount >= 100 && amount <= 1_000
+          ? 1_000
+          : 1;
+  const tokens = amount * scale;
+  return Number.isInteger(tokens) && tokens > 0
+    ? Math.min(1_000_000, Math.max(100_000, tokens))
+    : undefined;
+}
+
 // Claude caps the window at the model's context, so a setting at or above it never applies.
 function claudeAutoCompactThreshold(
   autoCompactWindow: number | undefined,
@@ -2628,7 +2650,7 @@ const decodeClaudeSubagentCacheSettings = Schema.decodeUnknownEffect(
     ),
   ),
 );
-const ClaudeAutoCompactWindowSetting = Schema.Union([Schema.Finite, Schema.Literal("auto")]);
+const ClaudeAutoCompactWindowSetting = Schema.Union([Schema.Int, Schema.Literal("auto")]);
 const ClaudeAutoCompactSettings = Schema.Struct({
   autoCompactWindow: Schema.optionalKey(ClaudeAutoCompactWindowSetting),
   modelSettings: Schema.optionalKey(
@@ -4623,15 +4645,24 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
     },
   );
 
-  // Claude Code's auto-compact window: its env var, then T3's setting (sent as flag settings), then
-  // --settings, then settings files. In one source, modelSettings.<model>.autoCompactWindow (what
-  // /autocompact writes) replaces the top-level value; "auto" keeps Claude's tuned window.
+  // Claude Code's auto-compact window: its env var, then --autocompact, then T3's setting (sent as
+  // flag settings), then --settings, then settings files. In one source,
+  // modelSettings.<model>.autoCompactWindow (what /autocompact writes) replaces the top-level
+  // value; "auto" keeps Claude's tuned window.
   const resolveAutoCompactWindow = Effect.fn("ClaudeAdapterV2.resolveAutoCompactWindow")(function* (
     cwd: string | null,
     modelSelection: ModelSelection,
   ) {
-    const fromEnvironment = Number(adapterOptions.environment.CLAUDE_CODE_AUTO_COMPACT_WINDOW);
-    if (fromEnvironment > 0) return fromEnvironment;
+    const fromEnvironment = parseClaudeAutoCompactWindow(
+      adapterOptions.environment.CLAUDE_CODE_AUTO_COMPACT_WINDOW,
+      "env",
+    );
+    if (typeof fromEnvironment === "number") return fromEnvironment;
+    const fromFlag = parseClaudeAutoCompactWindow(
+      parseCliArgs(adapterOptions.settings.launchArgs).flags.autocompact,
+      "flag",
+    );
+    if (fromFlag !== undefined) return fromFlag === "auto" ? undefined : fromFlag;
     const fromT3 = Number(adapterOptions.settings.autoCompactWindow);
     if (fromT3 > 0) return fromT3;
     const model = compileClaudeModelSelection(modelSelection).apiModelId.replace(/\[1m\]$/i, "");
diff --git a/apps/web/src/lib/contextWindow.test.ts b/apps/web/src/lib/contextWindow.test.ts
index b9f52f208239..08a4cc50efe7 100644
--- a/apps/web/src/lib/contextWindow.test.ts
+++ b/apps/web/src/lib/contextWindow.test.ts
@@ -149,7 +149,8 @@ describe("latestProviderTurnTokenUsage", () => {
       const providerThread = {
         contextUsage: {
           usedTokens,
-          maxTokens: 200_000,
+          maxTokens: 1_000_000,
+          autoCompactThreshold: 200_000,
           cost: { amount: 0.42, currency: "USD" },
         },
         updatedAt: DateTime.makeUnsafe("2026-10-19T12:10:00.000Z"),
@@ -160,6 +161,7 @@ describe("latestProviderTurnTokenUsage", () => {
       expect(snapshot).toMatchObject({
         usedTokens,
         maxTokens: 200_000,
+        remainingTokens: 200_000 - usedTokens,
         cost: { amount: 0.42, currency: "USD" },
         updatedAt: "2026-10-19T12:10:00.000Z",
       });

From 4a16f3c2b8d768f1645af6c2dc76e4428b52c4e4 Mon Sep 17 00:00:00 2001
From: Per <123196452+noxaur@users.noreply.github.com>
Date: Fri, 30 Oct 2026 22:31:55 +0100
Subject: [PATCH 3/7] fix(claude): limit the window lookup to Claude's settings
 files

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 .../Adapters/ClaudeAdapterV2.test.ts          | 51 +---------------
 .../Adapters/ClaudeAdapterV2.ts               | 61 +++----------------
 2 files changed, 11 insertions(+), 101 deletions(-)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 8608ffc5ca19..50762f3f1982 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -6359,8 +6359,6 @@ describe("ClaudeAdapterV2 background wake turns", () => {
     threshold: number | undefined;
     userSettings?: string;
     projectSettings?: string;
-    launchArgs?: string;
-    environment?: NodeJS.ProcessEnv;
   }>([
     { autoCompactWindow: "", model: "claude-sonnet-4-6", threshold: undefined },
     { autoCompactWindow: "150000", model: "claude-sonnet-4-6", threshold: 150_000 },
@@ -6389,13 +6387,6 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       projectSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":"auto"}}}',
       threshold: undefined,
     },
-    {
-      autoCompactWindow: "",
-      model: "claude-opus-5-5",
-      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
-      launchArgs: `--settings '{"autoCompactWindow":250000}'`,
-      threshold: 250_000,
-    },
     {
       autoCompactWindow: "250000",
       model: "claude-opus-5-5",
@@ -6408,46 +6399,9 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       userSettings: '{"autoCompactWindow":150000.5}',
       threshold: undefined,
     },
-    // --autocompact reads 100 to 1000 as thousands and beats T3's setting and settings files.
-    {
-      autoCompactWindow: "300000",
-      model: "claude-opus-5-5",
-      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
-      launchArgs: "--autocompact 250",
-      threshold: 250_000,
-    },
-    {
-      autoCompactWindow: "",
-      model: "claude-opus-5-5",
-      userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
-      launchArgs: "--autocompact auto",
-      threshold: undefined,
-    },
-    // The env var beats every other source, takes k/M suffixes, and clamps to 100k.
-    {
-      autoCompactWindow: "",
-      model: "claude-opus-5-5",
-      launchArgs: "--autocompact 250k",
-      environment: { CLAUDE_CODE_AUTO_COMPACT_WINDOW: "200k" },
-      threshold: 200_000,
-    },
-    {
-      autoCompactWindow: "",
-      model: "claude-opus-5-5",
-      environment: { CLAUDE_CODE_AUTO_COMPACT_WINDOW: "200" },
-      threshold: 100_000,
-    },
   ])(
     "ignores stale snapshots after compaction and reports threshold $threshold for $model",
-    ({
-      autoCompactWindow,
-      model,
-      threshold,
-      userSettings = "{}",
-      projectSettings,
-      launchArgs = "",
-      environment,
-    }) =>
+    ({ autoCompactWindow, model, threshold, userSettings = "{}", projectSettings }) =>
       Effect.gen(function* () {
         const fileSystem = yield* FileSystem.FileSystem;
         const path = yield* Path.Path;
@@ -6462,8 +6416,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
           );
         }
         const harness = yield* makeWakeHarnessWithOptions({
-          settings: { ...DEFAULT_CLAUDE_SETTINGS, autoCompactWindow, homePath: home, launchArgs },
-          ...(environment === undefined ? {} : { environment }),
+          settings: { ...DEFAULT_CLAUDE_SETTINGS, autoCompactWindow, homePath: home },
         });
         yield* harness.runtime.startTurn(
           makeClaudeTestTurnInput({
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 2970265d5025..71afb4c14d94 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -233,28 +233,6 @@ function claudePromptCacheTtlMs(
   return undefined;
 }
 
-// Claude reads a token count or a k/M suffix and clamps it to 100k-1M. Only --autocompact also
-// takes "auto" and reads 100 to 1000 as thousands.
-function parseClaudeAutoCompactWindow(raw: string | null | undefined, source: "env" | "flag") {
-  const value = raw?.trim().toLowerCase();
-  if (value === "auto") return source === "flag" ? "auto" : undefined;
-  const match = value === undefined ? null : /^(\d+(?:\.\d+)?)([km])?$/.exec(value);
-  if (match === null) return undefined;
-  const amount = Number(match[1]);
-  const scale =
-    match[2] === "k"
-      ? 1_000
-      : match[2] === "m"
-        ? 1_000_000
-        : source === "flag" && amount >= 100 && amount <= 1_000
-          ? 1_000
-          : 1;
-  const tokens = amount * scale;
-  return Number.isInteger(tokens) && tokens > 0
-    ? Math.min(1_000_000, Math.max(100_000, tokens))
-    : undefined;
-}
-
 // Claude caps the window at the model's context, so a setting at or above it never applies.
 function claudeAutoCompactThreshold(
   autoCompactWindow: number | undefined,
@@ -2660,8 +2638,7 @@ const ClaudeAutoCompactSettings = Schema.Struct({
     ),
   ),
 });
-const decodeClaudeAutoCompactSettings = Schema.decodeUnknownOption(ClaudeAutoCompactSettings);
-const decodeClaudeAutoCompactSettingsFile = Schema.decodeUnknownEffect(
+const decodeClaudeAutoCompactSettings = Schema.decodeUnknownEffect(
   fromLenientJson(ClaudeAutoCompactSettings),
 );
 const decodeClaudeEnvSettings = Schema.decodeUnknownEffect(
@@ -4645,46 +4622,26 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
     },
   );
 
-  // Claude Code's auto-compact window: its env var, then --autocompact, then T3's setting (sent as
-  // flag settings), then --settings, then settings files. In one source,
+  // T3's setting is sent as flag settings, so it beats every settings file. In one file,
   // modelSettings.<model>.autoCompactWindow (what /autocompact writes) replaces the top-level
   // value; "auto" keeps Claude's tuned window.
   const resolveAutoCompactWindow = Effect.fn("ClaudeAdapterV2.resolveAutoCompactWindow")(function* (
     cwd: string | null,
     modelSelection: ModelSelection,
   ) {
-    const fromEnvironment = parseClaudeAutoCompactWindow(
-      adapterOptions.environment.CLAUDE_CODE_AUTO_COMPACT_WINDOW,
-      "env",
-    );
-    if (typeof fromEnvironment === "number") return fromEnvironment;
-    const fromFlag = parseClaudeAutoCompactWindow(
-      parseCliArgs(adapterOptions.settings.launchArgs).flags.autocompact,
-      "flag",
-    );
-    if (fromFlag !== undefined) return fromFlag === "auto" ? undefined : fromFlag;
     const fromT3 = Number(adapterOptions.settings.autoCompactWindow);
     if (fromT3 > 0) return fromT3;
     const model = compileClaudeModelSelection(modelSelection).apiModelId.replace(/\[1m\]$/i, "");
-    const windowIn = (settings: typeof ClaudeAutoCompactSettings.Type | undefined) =>
-      settings?.modelSettings?.[model]?.autoCompactWindow ?? settings?.autoCompactWindow;
-    const launchArgSettings = yield* readClaudeLaunchArgSettings({
-      settings: adapterOptions.settings,
-      cwd,
-      fileSystem,
-      path,
-    }).pipe(Effect.orElseSucceed(() => undefined));
-    let value = windowIn(Option.getOrUndefined(decodeClaudeAutoCompactSettings(launchArgSettings)));
     for (const settingsFile of yield* settingsFilesByPrecedence(cwd)) {
-      if (value !== undefined) break;
-      value = windowIn(
-        yield* fileSystem.readFileString(settingsFile).pipe(
-          Effect.flatMap(decodeClaudeAutoCompactSettingsFile),
-          Effect.orElseSucceed(() => undefined),
-        ),
+      const settings = yield* fileSystem.readFileString(settingsFile).pipe(
+        Effect.flatMap(decodeClaudeAutoCompactSettings),
+        Effect.orElseSucceed(() => undefined),
       );
+      const value =
+        settings?.modelSettings?.[model]?.autoCompactWindow ?? settings?.autoCompactWindow;
+      if (value !== undefined) return value === "auto" ? undefined : value;
     }
-    return value === "auto" ? undefined : value;
+    return undefined;
   });
 
   const userInvocableSkills = (cwd: string | null) =>

From a643c48fac029d5ade4ef29b8a4454758beb4632 Mon Sep 17 00:00:00 2001
From: Per <123196452+noxaur@users.noreply.github.com>
Date: Fri, 30 Oct 2026 23:01:10 +0100
Subject: [PATCH 4/7] fix(claude): a bad modelSettings entry no longer hides
 the window

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 .../Adapters/ClaudeAdapterV2.test.ts          |  2 +-
 .../Adapters/ClaudeAdapterV2.ts               | 32 ++++++++++++-------
 2 files changed, 21 insertions(+), 13 deletions(-)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 50762f3f1982..92c3744c7f1c 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -6370,7 +6370,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       autoCompactWindow: "",
       model: "claude-opus-5-5",
       userSettings:
-        '{"autoCompactWindow":300000,"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
+        '{"autoCompactWindow":300000,"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000},"claude-sonnet-5-5":{"autoCompactWindow":"big"}}}',
       threshold: 400_000,
     },
     {
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 71afb4c14d94..33635dcf5c60 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -2629,18 +2629,19 @@ const decodeClaudeSubagentCacheSettings = Schema.decodeUnknownEffect(
   ),
 );
 const ClaudeAutoCompactWindowSetting = Schema.Union([Schema.Int, Schema.Literal("auto")]);
-const ClaudeAutoCompactSettings = Schema.Struct({
-  autoCompactWindow: Schema.optionalKey(ClaudeAutoCompactWindowSetting),
-  modelSettings: Schema.optionalKey(
-    Schema.Record(
-      Schema.String,
-      Schema.Struct({ autoCompactWindow: Schema.optionalKey(ClaudeAutoCompactWindowSetting) }),
-    ),
-  ),
-});
+// Values are checked one at a time, so a bad entry for another model can't hide this one.
 const decodeClaudeAutoCompactSettings = Schema.decodeUnknownEffect(
-  fromLenientJson(ClaudeAutoCompactSettings),
+  fromLenientJson(
+    Schema.Struct({
+      autoCompactWindow: Schema.optionalKey(Schema.Unknown),
+      modelSettings: Schema.optionalKey(Schema.Record(Schema.String, Schema.Unknown)),
+    }),
+  ),
+);
+const decodeClaudeModelAutoCompactSettings = Schema.decodeUnknownOption(
+  Schema.Struct({ autoCompactWindow: ClaudeAutoCompactWindowSetting }),
 );
+const decodeClaudeAutoCompactWindow = Schema.decodeUnknownOption(ClaudeAutoCompactWindowSetting);
 const decodeClaudeEnvSettings = Schema.decodeUnknownEffect(
   fromLenientJson(
     Schema.StructWithRest(
@@ -4637,8 +4638,15 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
         Effect.flatMap(decodeClaudeAutoCompactSettings),
         Effect.orElseSucceed(() => undefined),
       );
-      const value =
-        settings?.modelSettings?.[model]?.autoCompactWindow ?? settings?.autoCompactWindow;
+      const value = Option.getOrUndefined(
+        Option.orElse(
+          Option.map(
+            decodeClaudeModelAutoCompactSettings(settings?.modelSettings?.[model]),
+            (entry) => entry.autoCompactWindow,
+          ),
+          () => decodeClaudeAutoCompactWindow(settings?.autoCompactWindow),
+        ),
+      );
       if (value !== undefined) return value === "auto" ? undefined : value;
     }
     return undefined;

From 09c5ad727f759462e3f590ed8a060e4e53e55b04 Mon Sep 17 00:00:00 2001
From: Per <123196452+noxaur@users.noreply.github.com>
Date: Sat, 31 Oct 2026 02:48:17 +0100
Subject: [PATCH 5/7] fix(claude): report the auto-compact window as the
 context size

Like Claude's /context, the meter measures usage against the window, so
the web change is no longer needed. The window is also read before the
query opens.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 .../Adapters/ClaudeAdapterV2.test.ts          | 47 +++++++++++++++----
 .../Adapters/ClaudeAdapterV2.ts               | 25 +++++-----
 apps/web/src/lib/contextWindow.test.ts        | 10 ++--
 apps/web/src/lib/contextWindow.ts             |  6 +--
 4 files changed, 58 insertions(+), 30 deletions(-)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 5e8aea9ec4d0..43a710c7b331 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -6517,14 +6517,35 @@ describe("ClaudeAdapterV2 background wake turns", () => {
     autoCompactWindow: string;
     model: string;
     threshold: number | undefined;
+    maxTokens: number;
     userSettings?: string;
     projectSettings?: string;
   }>([
-    { autoCompactWindow: "", model: "claude-sonnet-4-6", threshold: undefined },
-    { autoCompactWindow: "150000", model: "claude-sonnet-4-6", threshold: 117_000 },
-    { autoCompactWindow: "200000", model: "claude-sonnet-4-6", threshold: undefined },
-    { autoCompactWindow: "650000", model: "claude-sonnet-4-6", threshold: undefined },
-    { autoCompactWindow: "650000", model: "uncatalogued-model", threshold: 617_000 },
+    { autoCompactWindow: "", model: "claude-sonnet-4-6", threshold: undefined, maxTokens: 200_000 },
+    {
+      autoCompactWindow: "150000",
+      model: "claude-sonnet-4-6",
+      threshold: 117_000,
+      maxTokens: 150_000,
+    },
+    {
+      autoCompactWindow: "200000",
+      model: "claude-sonnet-4-6",
+      threshold: undefined,
+      maxTokens: 200_000,
+    },
+    {
+      autoCompactWindow: "650000",
+      model: "claude-sonnet-4-6",
+      threshold: undefined,
+      maxTokens: 200_000,
+    },
+    {
+      autoCompactWindow: "650000",
+      model: "uncatalogued-model",
+      threshold: 617_000,
+      maxTokens: 650_000,
+    },
     // /autocompact writes the per-model value, which beats the file's top-level one.
     {
       autoCompactWindow: "",
@@ -6532,6 +6553,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       userSettings:
         '{"autoCompactWindow":300000,"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000},"claude-sonnet-5-5":{"autoCompactWindow":"big"}}}',
       threshold: 367_000,
+      maxTokens: 400_000,
     },
     {
       autoCompactWindow: "",
@@ -6539,6 +6561,7 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
       projectSettings: '{"autoCompactWindow":300000}',
       threshold: 267_000,
+      maxTokens: 300_000,
     },
     {
       autoCompactWindow: "",
@@ -6546,22 +6569,25 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       userSettings: '{"autoCompactWindow":300000}',
       projectSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":"auto"}}}',
       threshold: undefined,
+      maxTokens: 1_000_000,
     },
     {
       autoCompactWindow: "250000",
       model: "claude-opus-5-5",
       userSettings: '{"modelSettings":{"claude-opus-5-5":{"autoCompactWindow":400000}}}',
       threshold: 217_000,
+      maxTokens: 250_000,
     },
     {
       autoCompactWindow: "",
       model: "claude-opus-5-5",
       userSettings: '{"autoCompactWindow":150000.5}',
       threshold: undefined,
+      maxTokens: 1_000_000,
     },
   ])(
     "ignores stale snapshots after compaction and reports threshold $threshold for $model",
-    ({ autoCompactWindow, model, threshold, userSettings = "{}", projectSettings }) =>
+    ({ autoCompactWindow, model, threshold, maxTokens, userSettings = "{}", projectSettings }) =>
       Effect.gen(function* () {
         const fileSystem = yield* FileSystem.FileSystem;
         const path = yield* Path.Path;
@@ -6619,10 +6645,15 @@ describe("ClaudeAdapterV2 background wake turns", () => {
         assert.deepEqual(
           harness.events.flatMap((event) =>
             event.type === "provider_turn.updated" && event.providerTurn.tokenUsage
-              ? [event.providerTurn.tokenUsage.autoCompactThreshold]
+              ? [
+                  [
+                    event.providerTurn.tokenUsage.maxTokens,
+                    event.providerTurn.tokenUsage.autoCompactThreshold,
+                  ],
+                ]
               : [],
           ),
-          [threshold, threshold, threshold],
+          Array.from({ length: 3 }, () => [maxTokens, threshold]),
         );
       }).pipe(
         Effect.provide(
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 846a9187a2d0..5521d5e9ceab 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -238,15 +238,20 @@ function claudePromptCacheTtlMs(
 // getContextUsage reports a 150,000 window as a 117,000 threshold, for every catalog model.
 const CLAUDE_AUTO_COMPACT_RESERVE_TOKENS = 33_000;
 
-function claudeAutoCompactThreshold(
+// Like Claude's /context, measure usage against the window when it is below the model's.
+function claudeContextLimits(
   autoCompactWindow: number | undefined,
-  maxTokens: number | null,
+  modelSelection: ModelSelection,
 ) {
+  const contextWindow = claudeContextWindow(modelSelection);
   return autoCompactWindow !== undefined &&
     autoCompactWindow > 0 &&
-    (maxTokens === null || autoCompactWindow < maxTokens)
-    ? { autoCompactThreshold: autoCompactWindow - CLAUDE_AUTO_COMPACT_RESERVE_TOKENS }
-    : {};
+    (contextWindow === null || autoCompactWindow < contextWindow)
+    ? {
+        maxTokens: autoCompactWindow,
+        autoCompactThreshold: autoCompactWindow - CLAUDE_AUTO_COMPACT_RESERVE_TOKENS,
+      }
+    : { maxTokens: contextWindow };
 }
 
 function claudeMessageInputTokens(usage: {
@@ -277,7 +282,6 @@ export function claudeProviderTurnTokenUsage(
   const inputTokens = claudeMessageInputTokens(usage);
   const outputTokens = usage.output_tokens;
   const promptCacheTtlMs = claudePromptCacheTtlMs(usage.cache_creation);
-  const maxTokens = claudeContextWindow(modelSelection);
   // The cache lifetime starts with the request, not when its response ends.
   const promptCacheExpiresAt =
     promptCacheTtlMs === undefined || requestedAt === undefined
@@ -285,13 +289,12 @@ export function claudeProviderTurnTokenUsage(
       : DateTime.formatIso(DateTime.add(requestedAt, { milliseconds: promptCacheTtlMs }));
   return {
     usedTokens: inputTokens + outputTokens,
-    maxTokens,
+    ...claudeContextLimits(autoCompactWindow, modelSelection),
     inputTokens,
     cachedInputTokens: usage.cache_read_input_tokens ?? 0,
     outputTokens,
     reasoningOutputTokens: 0,
     ...(promptCacheTtlMs === undefined ? {} : { promptCacheTtlMs }),
-    ...claudeAutoCompactThreshold(autoCompactWindow, maxTokens),
     ...(promptCacheExpiresAt === undefined ? {} : { promptCacheExpiresAt }),
     updatedAt,
   };
@@ -8642,7 +8645,6 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
                 ? Math.round(postTokens)
                 : undefined;
             if (afterTokenCount !== undefined) {
-              const maxTokens = claudeContextWindow(context.input.modelSelection);
               yield* emitProviderEvent({
                 type: "provider_turn.updated",
                 driver: CLAUDE_PROVIDER,
@@ -8663,8 +8665,7 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
                   completedAt: null,
                   tokenUsage: {
                     usedTokens: afterTokenCount,
-                    maxTokens,
-                    ...claudeAutoCompactThreshold(context.autoCompactWindow, maxTokens),
+                    ...claudeContextLimits(context.autoCompactWindow, context.input.modelSelection),
                     updatedAt: DateTime.formatIso(now),
                   },
                 },
@@ -10477,11 +10478,11 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
                     Effect.provideService(ChildProcessSpawner.ChildProcessSpawner, spawner),
                     Effect.provideService(Path.Path, path),
                   );
-            const querySession = yield* openQuery(turnInput, nativeThreadId);
             const autoCompactWindow = yield* resolveAutoCompactWindow(
               turnInput.runtimePolicy.cwd,
               turnInput.modelSelection,
             );
+            const querySession = yield* openQuery(turnInput, nativeThreadId);
             const context: ActiveClaudeTurnContext = {
               input: turnInput,
               autoCompactWindow,
diff --git a/apps/web/src/lib/contextWindow.test.ts b/apps/web/src/lib/contextWindow.test.ts
index 08a4cc50efe7..c27ddd9a0465 100644
--- a/apps/web/src/lib/contextWindow.test.ts
+++ b/apps/web/src/lib/contextWindow.test.ts
@@ -60,9 +60,9 @@ describe("live provider-turn usage (#8144)", () => {
     const snapshot = deriveLatestContextWindowSnapshot([], usage);
     expect(snapshot).not.toBeNull();
     expect(snapshot?.usedTokens).toBe(42_000);
-    expect(snapshot?.maxTokens).toBe(150_000);
-    expect(snapshot?.remainingTokens).toBe(108_000);
-    expect(snapshot?.usedPercentage).toBeCloseTo(28);
+    expect(snapshot?.maxTokens).toBe(200_000);
+    expect(snapshot?.remainingTokens).toBe(158_000);
+    expect(snapshot?.usedPercentage).toBe(21);
     expect(snapshot?.autoCompactThreshold).toBe(150_000);
     expect(
       formatContextWindowCompactionMessage("Claude Sonnet 4.6", snapshot?.autoCompactThreshold),
@@ -149,8 +149,7 @@ describe("latestProviderTurnTokenUsage", () => {
       const providerThread = {
         contextUsage: {
           usedTokens,
-          maxTokens: 1_000_000,
-          autoCompactThreshold: 200_000,
+          maxTokens: 200_000,
           cost: { amount: 0.42, currency: "USD" },
         },
         updatedAt: DateTime.makeUnsafe("2026-10-19T12:10:00.000Z"),
@@ -161,7 +160,6 @@ describe("latestProviderTurnTokenUsage", () => {
       expect(snapshot).toMatchObject({
         usedTokens,
         maxTokens: 200_000,
-        remainingTokens: 200_000 - usedTokens,
         cost: { amount: 0.42, currency: "USD" },
         updatedAt: "2026-10-19T12:10:00.000Z",
       });
diff --git a/apps/web/src/lib/contextWindow.ts b/apps/web/src/lib/contextWindow.ts
index a04a434f9462..8c449249e033 100644
--- a/apps/web/src/lib/contextWindow.ts
+++ b/apps/web/src/lib/contextWindow.ts
@@ -63,8 +63,7 @@ export function deriveLatestContextWindowSnapshot(
 ): ContextWindowSnapshot | null {
   if (liveUsage != null) {
     const usedTokens = Math.max(0, liveUsage.usedTokens);
-    // Like Claude's /context, measure against the auto-compact window when it is smaller.
-    const maxTokens = liveUsage.autoCompactThreshold ?? liveUsage.maxTokens ?? null;
+    const maxTokens = liveUsage.maxTokens ?? null;
     const usedPercentage =
       maxTokens !== null && maxTokens > 0 ? Math.min(100, (usedTokens / maxTokens) * 100) : null;
     const remainingTokens =
@@ -101,8 +100,7 @@ export function deriveLatestContextWindowSnapshot(
     providerUsage !== undefined &&
     providerUsageUpdatedAt !== undefined
   ) {
-    const maxTokens =
-      asFiniteNumber(providerUsage.autoCompactThreshold) ?? asFiniteNumber(providerUsage.maxTokens);
+    const maxTokens = asFiniteNumber(providerUsage.maxTokens);
     const usedTokens = providerUsage.usedTokens;
     const usedPercentage =
       maxTokens !== null && maxTokens > 0 ? Math.min(100, (usedTokens / maxTokens) * 100) : null;

From 6b67472f1634dc001f89ac846b422359b57f9454 Mon Sep 17 00:00:00 2001
From: maria-rcks <maria@kuuro.net>
Date: Wed, 4 Nov 2026 02:09:01 +0000
Subject: [PATCH 6/7] fix(claude): validate saved windows and match catalog
 aliases

---
 .../Adapters/ClaudeAdapterV2.test.ts          | 14 +++++++++++
 .../Adapters/ClaudeAdapterV2.ts               | 24 ++++++++++++-------
 2 files changed, 30 insertions(+), 8 deletions(-)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index 48fdd982f6ef..a0430443c9a6 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -7308,6 +7308,20 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       threshold: 617_000,
       maxTokens: 650_000,
     },
+    ...[1, 50_000, 1_000_001].map((window) => ({
+      autoCompactWindow: "",
+      model: "claude-sonnet-4-6",
+      userSettings: JSON.stringify({ autoCompactWindow: window }),
+      threshold: undefined,
+      maxTokens: 200_000,
+    })),
+    {
+      autoCompactWindow: "",
+      model: "claude-sonnet-4-6",
+      userSettings: '{"modelSettings":{"claude-sonnet-4-6-20251117":{"autoCompactWindow":150000}}}',
+      threshold: 117_000,
+      maxTokens: 150_000,
+    },
     // /autocompact writes the per-model value, which beats the file's top-level one.
     {
       autoCompactWindow: "",
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index adecd49cc0b4..18369ca4f280 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -2745,7 +2745,10 @@ const decodeClaudeSubagentCacheSettings = Schema.decodeUnknownEffect(
     ),
   ),
 );
-const ClaudeAutoCompactWindowSetting = Schema.Union([Schema.Int, Schema.Literal("auto")]);
+const ClaudeAutoCompactWindowSetting = Schema.Union([
+  Schema.Int.check(Schema.isBetween({ minimum: 100_000, maximum: 1_000_000 })),
+  Schema.Literal("auto"),
+]);
 // Values are checked one at a time, so a bad entry for another model can't hide this one.
 const decodeClaudeAutoCompactSettings = Schema.decodeUnknownEffect(
   fromLenientJson(
@@ -4801,14 +4804,19 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
         Effect.flatMap(decodeClaudeAutoCompactSettings),
         Effect.orElseSucceed(() => undefined),
       );
+      for (const [key, entry] of Object.entries(settings?.modelSettings ?? {})) {
+        const entryModel = compileClaudeModelSelection({
+          ...modelSelection,
+          model: key,
+        }).apiModelId.replace(/\[1m\]$/i, "");
+        if (entryModel !== model) continue;
+        const window = Option.getOrUndefined(decodeClaudeModelAutoCompactSettings(entry));
+        if (window !== undefined) {
+          return window.autoCompactWindow === "auto" ? undefined : window.autoCompactWindow;
+        }
+      }
       const value = Option.getOrUndefined(
-        Option.orElse(
-          Option.map(
-            decodeClaudeModelAutoCompactSettings(settings?.modelSettings?.[model]),
-            (entry) => entry.autoCompactWindow,
-          ),
-          () => decodeClaudeAutoCompactWindow(settings?.autoCompactWindow),
-        ),
+        decodeClaudeAutoCompactWindow(settings?.autoCompactWindow),
       );
       if (value !== undefined) return value === "auto" ? undefined : value;
     }

From 8882f7cce215beafa6aa9b43733bdc577488ee7b Mon Sep 17 00:00:00 2001
From: maria-rcks <maria@kuuro.net>
Date: Wed, 4 Nov 2026 02:12:08 +0000
Subject: [PATCH 7/7] fix(claude): prefer canonical saved model windows

---
 .../src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts | 8 ++++++++
 .../src/orchestration-v2/Adapters/ClaudeAdapterV2.ts      | 6 ++++++
 2 files changed, 14 insertions(+)

diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index a0430443c9a6..e6d742bf17c3 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -7322,6 +7322,14 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       threshold: 117_000,
       maxTokens: 150_000,
     },
+    {
+      autoCompactWindow: "",
+      model: "claude-sonnet-4-6",
+      userSettings:
+        '{"modelSettings":{"claude-sonnet-4-6-20251117":{"autoCompactWindow":150000},"claude-sonnet-4-6":{"autoCompactWindow":180000}}}',
+      threshold: 147_000,
+      maxTokens: 180_000,
+    },
     // /autocompact writes the per-model value, which beats the file's top-level one.
     {
       autoCompactWindow: "",
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 18369ca4f280..ac41559fcfbe 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -4804,6 +4804,12 @@ export const makeClaudeAdapterV2 = Effect.fn("makeClaudeAdapterV2")(function* (
         Effect.flatMap(decodeClaudeAutoCompactSettings),
         Effect.orElseSucceed(() => undefined),
       );
+      const canonical = Option.getOrUndefined(
+        decodeClaudeModelAutoCompactSettings(settings?.modelSettings?.[model]),
+      );
+      if (canonical !== undefined) {
+        return canonical.autoCompactWindow === "auto" ? undefined : canonical.autoCompactWindow;
+      }
       for (const [key, entry] of Object.entries(settings?.modelSettings ?? {})) {
         const entryModel = compileClaudeModelSelection({
           ...modelSelection,