diff --git a/packages/core/src/core/coreToolScheduler.test.ts b/packages/core/src/core/coreToolScheduler.test.ts
index b02fe0c37..04dfdb378 100644
--- a/packages/core/src/core/coreToolScheduler.test.ts
+++ b/packages/core/src/core/coreToolScheduler.test.ts
@@ -4383,6 +4383,32 @@ describe('extractToolFilePaths', () => {
     ).toEqual([]);
   });
 
+  it('extracts pattern for glob (path-shaped selector, glob-only)', () => {
+    // Regression: `glob({ pattern: 'src/**/*.tsx' })` with no `path` is a
+    // common shape that previously produced an empty candidate set, so a
+    // skill keyed on `paths: ['src/**/*.tsx']` would never activate from
+    // a glob call.
+    expect(extractToolFilePaths('glob', { pattern: 'src/**/*.tsx' })).toEqual([
+      'src/**/*.tsx',
+    ]);
+    // Both `path` (search root) and `pattern` (selector) when both
+    // present.
+    expect(
+      extractToolFilePaths('glob', { path: 'src', pattern: '**/*.ts' }),
+    ).toEqual(['src', '**/*.ts']);
+  });
+
+  it('does not extract pattern for non-glob tools', () => {
+    // Grep's `pattern` is a regex, not a path glob; treating it as a
+    // path would false-match. Pattern is only path-shaped for `glob`.
+    expect(
+      extractToolFilePaths('grep_search', {
+        pattern: 'TODO|FIXME',
+        filePath: '/proj/a.ts',
+      }),
+    ).toEqual(['/proj/a.ts']);
+  });
+
   it('returns empty for tool names outside the FS allowlist', () => {
     // Regression: MCP tools and other non-FS tools that happen to use
     // `path` / `paths` for non-filesystem semantics (e.g. URL routes,
diff --git a/packages/core/src/core/coreToolScheduler.ts b/packages/core/src/core/coreToolScheduler.ts
index 9adc11508..3e00231cc 100644
--- a/packages/core/src/core/coreToolScheduler.ts
+++ b/packages/core/src/core/coreToolScheduler.ts
@@ -207,13 +207,24 @@ const FS_PATH_TOOL_NAMES: ReadonlySet<string> = new Set<string>([
  * Pull the filesystem path-bearing fields out of a tool's input. Different
  * core tools name these differently:
  *  - `file_path` — read-file, edit, write-file
- *  - `path`      — ls, ripGrep
+ *  - `path`      — ls (search root); glob (search root, optional)
  *  - `filePath`  — grep, lsp
  *  - `paths`     — ripGrep array form
+ *  - `pattern`   — glob (treated as a path-shaped glob, see below)
  * Used by ConditionalRulesRegistry / SkillActivationRegistry hooks to
  * route every path the tool just touched through the same activation
  * pipeline. Returns input order, with empty / non-string entries dropped.
  *
+ * For `glob` specifically, `pattern` is the actual selector — `path` is
+ * only the optional search root. `glob({ pattern: 'src/**\/*.tsx' })`
+ * with no `path` therefore needs `pattern` extracted, otherwise no
+ * conditional skill keyed on `paths: ['src/**\/*.tsx']` would ever
+ * activate from a glob call. The pattern goes through the same
+ * registry; picomatch matches glob-vs-glob on common shapes (e.g.
+ * `**\/*.tsx` matches `src/**\/*.tsx` because `**` accepts the
+ * literal `**` in the input). False matches are bounded to the same
+ * project-root scope as any other path.
+ *
  * Returns `[]` for tool names outside `FS_PATH_TOOL_NAMES` — see that
  * set's docstring for why this is gated rather than universal.
  */
@@ -235,6 +246,12 @@ export function extractToolFilePaths(
   if (Array.isArray(pathsField)) {
     for (const p of pathsField) push(p);
   }
+  if (toolName === ToolNames.GLOB) {
+    // Glob-only: include `pattern` as a path-shaped selector. Don't add
+    // it for grep_search even though grep also has a `pattern` field —
+    // grep's pattern is a regex, not a path glob, and would false-match.
+    push(obj['pattern']);
+  }
   return out;
 }
 
diff --git a/packages/core/src/skills/skill-activation.test.ts b/packages/core/src/skills/skill-activation.test.ts
index 6a14622e3..71cd81870 100644
--- a/packages/core/src/skills/skill-activation.test.ts
+++ b/packages/core/src/skills/skill-activation.test.ts
@@ -4,9 +4,11 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
+import * as path from 'node:path';
 import { describe, expect, it } from 'vitest';
 import {
   SkillActivationRegistry,
+  resolveProjectRelativePath,
   splitConditionalSkills,
 } from './skill-activation.js';
 import type { SkillConfig } from './types.js';
@@ -151,3 +153,51 @@ describe('SkillActivationRegistry', () => {
     expect(reg.activatedCount).toBe(0);
   });
 });
+
+describe('resolveProjectRelativePath', () => {
+  // Pure helper, exercised directly so the Windows-specific cross-drive
+  // branch is testable on POSIX CI runners. On a real POSIX host
+  // `path.win32` always behaves like Windows path semantics regardless
+  // of the host OS.
+  it('returns the forward-slash-normalized relative path for in-project files (POSIX)', () => {
+    expect(
+      resolveProjectRelativePath(
+        '/project/src/App.tsx',
+        '/project',
+        path.posix,
+      ),
+    ).toBe('src/App.tsx');
+  });
+
+  it('returns null for paths outside the project root (POSIX, `..` prefix)', () => {
+    expect(
+      resolveProjectRelativePath('/elsewhere/foo.ts', '/project', path.posix),
+    ).toBeNull();
+  });
+
+  it('returns null for Windows cross-drive paths (different drive letter)', () => {
+    // Direct exercise of the new `path.isAbsolute(rawRelativePath)`
+    // branch. `path.win32.relative('C:\\project', 'D:\\other\\file.ts')`
+    // returns an absolute string like `D:\\other\\file.ts` — without the
+    // isAbsolute guard, the helper would normalize the backslashes and
+    // return `D:/other/file.ts`, which would false-match a broad glob
+    // such as `**/*.ts`. Must return null instead.
+    expect(
+      resolveProjectRelativePath(
+        'D:\\other\\file.ts',
+        'C:\\project',
+        path.win32,
+      ),
+    ).toBeNull();
+  });
+
+  it('normalizes backslashes for in-project Windows paths', () => {
+    expect(
+      resolveProjectRelativePath(
+        'C:\\project\\src\\App.tsx',
+        'C:\\project',
+        path.win32,
+      ),
+    ).toBe('src/App.tsx');
+  });
+});
diff --git a/packages/core/src/skills/skill-activation.ts b/packages/core/src/skills/skill-activation.ts
index c0ff666c7..b0a809a3a 100644
--- a/packages/core/src/skills/skill-activation.ts
+++ b/packages/core/src/skills/skill-activation.ts
@@ -27,6 +27,35 @@ interface CompiledSkill {
   readonly matchers: picomatch.Matcher[];
 }
 
+/**
+ * Compute a project-relative, forward-slash-normalized path for matching
+ * against skill `paths:` globs, or `null` if the input falls outside the
+ * project root. Pure (no I/O), and parameterized over a `path` module so
+ * unit tests can pin the Windows-specific `path.win32` cross-drive case
+ * (where `path.relative('C:\\proj', 'D:\\elsewhere')` returns an
+ * absolute string that, after normalizing backslashes, would otherwise
+ * false-match a broad glob like `**\/*.ts`).
+ */
+export function resolveProjectRelativePath(
+  filePath: string,
+  projectRoot: string,
+  pathModule: typeof path = path,
+): string | null {
+  const absolutePath = pathModule.isAbsolute(filePath)
+    ? filePath
+    : pathModule.resolve(projectRoot, filePath);
+  const rawRelativePath = pathModule.relative(projectRoot, absolutePath);
+  if (
+    rawRelativePath === '..' ||
+    rawRelativePath.startsWith(`..${pathModule.sep}`) ||
+    rawRelativePath.startsWith('../') ||
+    pathModule.isAbsolute(rawRelativePath)
+  ) {
+    return null;
+  }
+  return rawRelativePath.replace(/\\/g, '/');
+}
+
 /**
  * Splits a skill list into unconditional skills (no `paths:`) and conditional
  * skills (with non-empty `paths:`). Unconditional skills are always offered to
@@ -79,30 +108,17 @@ export class SkillActivationRegistry {
   matchAndConsume(filePath: string): string[] {
     if (this.compiled.length === 0) return [];
 
-    const absolutePath = path.isAbsolute(filePath)
-      ? filePath
-      : path.resolve(this.projectRoot, filePath);
-    const rawRelativePath = path.relative(this.projectRoot, absolutePath);
-
-    // Skip files outside the project root — conditional skills are scoped to
-    // the project, matching ConditionalRulesRegistry's behavior.
-    //
-    // On Windows, `path.relative` between paths on different drives returns
-    // an absolute path (e.g. `D:\\other`), which would otherwise normalize
-    // to forward slashes and false-match a glob like `**/*.ts`. Reject
-    // absolute results before normalizing.
-    if (
-      rawRelativePath === '..' ||
-      rawRelativePath.startsWith(`..${path.sep}`) ||
-      rawRelativePath.startsWith('../') ||
-      path.isAbsolute(rawRelativePath)
-    ) {
+    // Skip files outside the project root — conditional skills are scoped
+    // to the project, matching ConditionalRulesRegistry's behavior. The
+    // helper handles the Windows cross-drive case (where `path.relative`
+    // returns an absolute string).
+    const relativePath = resolveProjectRelativePath(filePath, this.projectRoot);
+    if (relativePath === null) {
       debugLogger.debug(
-        `Skipping ${filePath}: outside project root (relative=${rawRelativePath})`,
+        `Skipping ${filePath}: outside project root or cross-drive`,
       );
       return [];
     }
-    const relativePath = rawRelativePath.replace(/\\/g, '/');
     debugLogger.debug(`matchAndConsume ${filePath} → relative=${relativePath}`);
 
     const newlyActivated: string[] = [];