diff --git a/docs/token-use.md b/docs/token-use.md
index f73bbb970..0fc4e170d 100644
--- a/docs/token-use.md
+++ b/docs/token-use.md
@@ -69,7 +69,7 @@ never show dollar cost.
 
 Provider prompt caching only applies within the cache TTL window. Clawdbot can
 optionally run **cache-ttl pruning**: it prunes the session once the cache TTL
-has expired, then resets the cache window so subsequent requests can re-use the
+has expired, then resets the cache window so subsequent requests can reuse the
 freshly cached context instead of re-caching the full history. This keeps cache
 write costs lower when a session goes idle past the TTL.
 
diff --git a/docs/tools/browser.md b/docs/tools/browser.md
index 3bf597e33..9160c0d8a 100644
--- a/docs/tools/browser.md
+++ b/docs/tools/browser.md
@@ -517,7 +517,7 @@ Notes:
   - Role snapshot options (`--interactive`, `--compact`, `--depth`, `--selector`) force a role-based snapshot with refs like `ref=e12`.
   - `--frame "<iframe selector>"` scopes role snapshots to an iframe (pairs with role refs like `e12`).
   - `--interactive` outputs a flat, easy-to-pick list of interactive elements (best for driving actions).
-  - `--labels` adds a viewport-only screenshot with overlayed ref labels (prints `MEDIA:<path>`).
+  - `--labels` adds a viewport-only screenshot with overlaid ref labels (prints `MEDIA:<path>`).
 - `click`/`type`/etc require a `ref` from `snapshot` (either numeric `12` or role ref `e12`).
   CSS selectors are intentionally not supported for actions.
 
@@ -534,7 +534,7 @@ Clawdbot supports two “snapshot” styles:
   - Output: a role-based list/tree with `[ref=e12]` (and optional `[nth=1]`).
   - Actions: `clawdbot browser click e12`, `clawdbot browser highlight e12`.
   - Internally, the ref is resolved via `getByRole(...)` (plus `nth()` for duplicates).
-  - Add `--labels` to include a viewport screenshot with overlayed `e12` labels.
+  - Add `--labels` to include a viewport screenshot with overlaid `e12` labels.
 
 Ref behavior:
 - Refs are **not stable across navigations**; if something fails, re-run `snapshot` and use a fresh ref.
diff --git a/extensions/open-prose/skills/prose/guidance/antipatterns.md b/extensions/open-prose/skills/prose/guidance/antipatterns.md
index fef0e41d0..a806b878f 100644
--- a/extensions/open-prose/skills/prose/guidance/antipatterns.md
+++ b/extensions/open-prose/skills/prose/guidance/antipatterns.md
@@ -568,7 +568,7 @@ session "You are a helpful assistant. Analyze this code for bugs."
 # ... later ...
 session "You are a helpful assistant. Analyze this code for bugs."
 # ... even later ...
-session "You are a helpful assistent. Analyze this code for bugs."  # Typo!
+session "You are a helpful assistant. Analyze this code for bugs."  # Typo!
 ```
 
 **Why it's bad**: Inconsistency when updating. Typos go unnoticed.
diff --git a/src/auto-reply/model.test.ts b/src/auto-reply/model.test.ts
index 4a5aa7714..462e97696 100644
--- a/src/auto-reply/model.test.ts
+++ b/src/auto-reply/model.test.ts
@@ -115,9 +115,9 @@ describe("extractModelDirective", () => {
 
   describe("edge cases", () => {
     it("absorbs path-like segments when /model includes extra slashes", () => {
-      const result = extractModelDirective("thats not /model gpt-5/tmp/hello");
+      const result = extractModelDirective("that's not /model gpt-5/tmp/hello");
       expect(result.hasDirective).toBe(true);
-      expect(result.cleaned).toBe("thats not");
+      expect(result.cleaned).toBe("that's not");
     });
 
     it("handles alias with special regex characters", () => {
diff --git a/src/auto-reply/reply.directive.parse.test.ts b/src/auto-reply/reply.directive.parse.test.ts
index 545c5e169..8de068c06 100644
--- a/src/auto-reply/reply.directive.parse.test.ts
+++ b/src/auto-reply/reply.directive.parse.test.ts
@@ -152,33 +152,33 @@ describe("directive parsing", () => {
   });
 
   it("preserves spacing when stripping think directives before paths", () => {
-    const res = extractThinkDirective("thats not /think high/tmp/hello");
+    const res = extractThinkDirective("that's not /think high/tmp/hello");
     expect(res.hasDirective).toBe(true);
-    expect(res.cleaned).toBe("thats not /tmp/hello");
+    expect(res.cleaned).toBe("that's not /tmp/hello");
   });
 
   it("preserves spacing when stripping verbose directives before paths", () => {
-    const res = extractVerboseDirective("thats not /verbose on/tmp/hello");
+    const res = extractVerboseDirective("that's not /verbose on/tmp/hello");
     expect(res.hasDirective).toBe(true);
-    expect(res.cleaned).toBe("thats not /tmp/hello");
+    expect(res.cleaned).toBe("that's not /tmp/hello");
   });
 
   it("preserves spacing when stripping reasoning directives before paths", () => {
-    const res = extractReasoningDirective("thats not /reasoning on/tmp/hello");
+    const res = extractReasoningDirective("that's not /reasoning on/tmp/hello");
     expect(res.hasDirective).toBe(true);
-    expect(res.cleaned).toBe("thats not /tmp/hello");
+    expect(res.cleaned).toBe("that's not /tmp/hello");
   });
 
   it("preserves spacing when stripping status directives before paths", () => {
-    const res = extractStatusDirective("thats not /status:/tmp/hello");
+    const res = extractStatusDirective("that's not /status:/tmp/hello");
     expect(res.hasDirective).toBe(true);
-    expect(res.cleaned).toBe("thats not /tmp/hello");
+    expect(res.cleaned).toBe("that's not /tmp/hello");
   });
 
   it("does not treat /usage as a status directive", () => {
-    const res = extractStatusDirective("thats not /usage:/tmp/hello");
+    const res = extractStatusDirective("that's not /usage:/tmp/hello");
     expect(res.hasDirective).toBe(false);
-    expect(res.cleaned).toBe("thats not /usage:/tmp/hello");
+    expect(res.cleaned).toBe("that's not /usage:/tmp/hello");
   });
 
   it("parses queue options and modes", () => {
diff --git a/src/commands/agent/session.ts b/src/commands/agent/session.ts
index 60860f0ec..a8c1d0616 100644
--- a/src/commands/agent/session.ts
+++ b/src/commands/agent/session.ts
@@ -65,7 +65,7 @@ export function resolveSessionKeyForRequest(opts: {
   let sessionKey: string | undefined =
     explicitSessionKey ?? (ctx ? resolveSessionKey(scope, ctx, mainKey) : undefined);
 
-  // If a session id was provided, prefer to re-use its entry (by id) even when no key was derived.
+  // If a session id was provided, prefer to reuse its entry (by id) even when no key was derived.
   if (
     !explicitSessionKey &&
     opts.sessionId &&