`glob` tool false-negatives on any multi-segment pattern unless prefixed with `**/`
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- Shell
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Description
## Describe the bug
The built-in `glob` tool returns "No files matched the pattern." for **any
pattern containing a path separator**, unless the pattern is prefixed with
`**/`. Literal relative paths (`2026/07/26.md`) and wildcarded multi-segment
patterns (`2026/07/*.md`) both fail even though the files exist directly under
the given `paths` root. Single-segment patterns (`inbox.md`, `*.md`) and
`**/`-prefixed patterns work.
This is worse than an inconvenience: the agent trusts the empty result. In one
session the agent checked for a file with its exact relative path, got no
match, and confidently declared the file missing — then acted on that false
premise.
## Affected version
1.0.70-0 (running as the VS Code Agent Sessions CLI backend; macOS arm64)
## Steps to reproduce the behavior
Against a repo containing `2026/07/26.md` and `inbox.md` at the root:
1. `glob` with `pattern: "2026/07/26.md"`, `paths: [""]` →
`No files matched the pattern.` (file exists)
2. `glob` with `pattern: "2026/07/*.md"`, same paths →
`No files matched the pattern.` (31 files exist there)
3. `glob` with `pattern: "**/07/26.md"`, same paths →
`/2026/07/26.md` ✔
4. `glob` with `pattern: "inbox.md"`, same paths →
`/inbox.md` ✔
So the failure is specifically: multi-segment pattern **not** prefixed with
`**/`. It looks like the matcher compares patterns against basenames (or a
single path segment) unless a globstar forces full-path matching.
## Expected behavior
A relative pattern is resolved against the given `paths` roots, per standard
glob semantics: `2026/07/26.md` matches `/2026/07/26.md`. At minimum,
the tool description should say patterns must be `**/`-prefixed to traverse
directories — but fixing the matching is much better than documenting the
trap, since empty results are treated as evidence of absence.
## Additional context
- OS: macOS 26.5.2, arm64
- Observed both from VS Code Agent Sessions and reproduced deterministically
(4 calls above, same session, seconds apart)
Contributor guide
Research direction
Start by locating the built-in glob tool and its path-matching implementation, then reproduce the four patterns from the issue against a repository containing the listed files. Trace how relative patterns are compared with the paths roots. Done means multi-segment relative patterns match existing files while the existing single-segment and **/ cases continue to work.
Written by the indexing model from the issue text.
Assessment
- Tech stack
- shell
- Domain
- cli, tooling
- Issue type
- Bug
- Difficulty
- 3/5
- Estimated time
- 1-2 days
- Activity status
- Quiet
- Clarity
- Mostly clear
- Newbie friendliness
- 55/100