bug: sandbox upload no longer preserves symlinks (regression from #1595) #2309

Agent Diagnostic

• Skills loaded: create-spike
• OpenShell version tested: 0.0.85-dev.5+g3dee5570
• Latest release checked: v0.0.83
• Known fixes reviewed: sandbox upload dereferences symlinks — uploaded as real directories, breaking git #1425 and merged PR fix(cli): preserve symlinks during sandbox upload #1595
• Possible duplicates reviewed: searched open issues for sandbox upload symlink; no open duplicate found. sandbox upload creates a directory instead of a file when source is inside a git repository #1740 concerns
  regular-file destination semantics and is unrelated.
• Findings: PR fix(cli): preserve symlinks during sandbox upload #1595 fixed symlink preservation in uploads. A later refactor in feat(providers): add Google Vertex AI inference provider #1568 restored Path::exists() and the Git-
  aware upload path for standalone sandbox upload. That path canonicalizes the source and dereferences symlinks. Dangling
  symlinks are rejected by the existence check.
• Remaining reason for filing: current main reproduces the regression, while the documentation promises that regular and
  dangling symlinks are preserved.

Description

Standalone openshell sandbox upload no longer preserves a symlink when the source path itself is a symlink.

Actual behavior: A symlink to a directory is uploaded as a real directory containing the target’s contents. A dangling
symlink is rejected as a missing local path.

Expected behavior: The sandbox should receive a symlink with the same target path. Dangling symlinks should also be
preserved, matching the documented behavior and the fix from #1595.

sandbox create --upload is not affected because it already uses the symlink-aware upload planner.

Reproduction Steps

1. Build the current CLI and create a sandbox:

OS="$(pwd)/target/release/openshell"
NAME="symlink-repro-$(date +%s)"
"$OS" sandbox create --name "$NAME" -- true

2. Create a Git repository containing a directory symlink and a dangling symlink:

tmp="$(mktemp -d)"
git -C "$tmp" init -q
mkdir "$tmp/real-dir"
echo hello > "$tmp/real-dir/file.txt"
ln -s real-dir "$tmp/link-dir"
git -C "$tmp" add real-dir link-dir
ln -s missing "$tmp/dangling"

3. Upload the directory symlink:

"$OS" sandbox upload "$NAME" "$tmp/link-dir" /sandbox/link-dir

4. Inspect the uploaded path:

"$OS" sandbox exec -n "$NAME" --no-tty -- test -L /sandbox/link-dir
echo "test -L exit=$?"

"$OS" sandbox exec -n "$NAME" --no-tty -- sh -c \
  'if [ -L /sandbox/link-dir ]; then echo SYMLINK; readlink /sandbox/link-dir; elif [ -d /sandbox/link-dir ]; then echo
  REAL_DIR; else echo OTHER; fi'

5. Try the dangling symlink:

"$OS" sandbox upload "$NAME" "$tmp/dangling" /sandbox/dangling

Environment

• OS: macOS 26.5.2, arm64
• Docker: 29.3.1
• OpenShell: 0.0.85-dev.5+g3dee5570
• Latest release checked: v0.0.83
• Possible duplicates checked: yes; no open duplicate found

Logs

Uploading .../link-dir -> sandbox:/sandbox/link-dir
  ✓ Upload complete
  test -L exit=1
  REAL_DIR
  

  For a dangling symlink:

  
  Error: local path does not exist: .../dangling

Agent-First Checklist

• I pointed my agent at the repo and had it investigate this issue
• I loaded relevant skills (e.g., debug-openshell-cluster, debug-inference, openshell-cli)
• I checked the latest OpenShell release and either reproduced the issue there or explained why I cannot upgrade/test it
• I searched existing issues for possible duplicates or explained why I could not
• My agent could not resolve this — the diagnostic above explains why