diff --git a/CHANGES b/CHANGES
index cd53ff93..a665f609 100644
--- a/CHANGES
+++ b/CHANGES
@@ -33,6 +33,14 @@ $ uvx --from 'vcspull' --prerelease allow vcspull
 
 _Upcoming changes will be written here._
 
+### Bug Fixes
+
+#### `vcspull add` keeps tilde workspace labels in path-first mode (#482, #483)
+
+- Running `vcspull add ~/study/python/…` from inside the workspace now logs the
+  workspace as `~/study/python/` instead of `./`, preserving tilde-shortened
+  labels for path-first imports.
+
 ## vcspull v1.45.0 (2025-11-02)
 
 ### Bug Fixes
diff --git a/src/vcspull/cli/add.py b/src/vcspull/cli/add.py
index c18b5bef..f79b5397 100644
--- a/src/vcspull/cli/add.py
+++ b/src/vcspull/cli/add.py
@@ -201,9 +201,10 @@ def handle_add_command(args: argparse.Namespace) -> None:
             repo_path,
         )
 
+    workspace_root_arg = getattr(args, "workspace_root_path", None)
     workspace_root_input = (
-        args.workspace_root_path
-        if getattr(args, "workspace_root_path", None)
+        workspace_root_arg
+        if workspace_root_arg is not None
         else repo_path.parent.as_posix()
     )
 
@@ -212,6 +213,7 @@ def handle_add_command(args: argparse.Namespace) -> None:
         workspace_path,
         cwd=cwd,
         home=pathlib.Path.home(),
+        preserve_cwd_label=workspace_root_arg in {".", "./"},
     )
 
     summary_url = display_url or config_url
@@ -479,11 +481,18 @@ def _aggregate_items(items: list[tuple[str, t.Any]]) -> dict[str, t.Any]:
         cwd=cwd,
     )
     workspace_label = workspace_map.get(workspace_path)
+
+    if workspace_root_path is None:
+        preserve_workspace_label = path is None
+    else:
+        preserve_workspace_label = workspace_root_path in {".", "./"}
+
     if workspace_label is None:
         workspace_label = workspace_root_label(
             workspace_path,
             cwd=cwd,
             home=home,
+            preserve_cwd_label=preserve_workspace_label,
         )
         workspace_map[workspace_path] = workspace_label
         raw_config.setdefault(workspace_label, {})
diff --git a/src/vcspull/config.py b/src/vcspull/config.py
index 6dc351e8..1c06e079 100644
--- a/src/vcspull/config.py
+++ b/src/vcspull/config.py
@@ -588,12 +588,13 @@ def workspace_root_label(
     *,
     cwd: pathlib.Path | None = None,
     home: pathlib.Path | None = None,
+    preserve_cwd_label: bool = True,
 ) -> str:
     """Create a normalized label for a workspace root path."""
     cwd = cwd or pathlib.Path.cwd()
     home = home or pathlib.Path.home()
 
-    if workspace_path == cwd:
+    if preserve_cwd_label and workspace_path == cwd:
         return "./"
 
     try:
diff --git a/tests/cli/test_add.py b/tests/cli/test_add.py
index 065d8f49..eddafd0f 100644
--- a/tests/cli/test_add.py
+++ b/tests/cli/test_add.py
@@ -890,3 +890,45 @@ def test_add_repo_no_merge_preserves_duplicate_sections(
     expected_repos = set(expected_original_repos) | {new_repo_name}
     assert combined_repos == expected_repos, f"{test_id}: repositories mismatch"
     assert contains_new_repo, f"{test_id}: new repo missing from duplicate sections"
+
+
+def test_handle_add_command_workspace_label_from_workspace_root(
+    tmp_path: pathlib.Path,
+    monkeypatch: MonkeyPatch,
+    caplog: t.Any,
+) -> None:
+    """CLI add should label workspace roots with their tilde path even from root cwd."""
+    caplog.set_level(logging.INFO)
+
+    monkeypatch.setenv("HOME", str(tmp_path))
+
+    workspace_root = tmp_path / "study/python"
+    repo_path = workspace_root / "pytest-docker"
+    init_git_repo(repo_path, remote_url="https://github.com/avast/pytest-docker")
+
+    monkeypatch.chdir(workspace_root)
+
+    config_file = tmp_path / ".vcspull.yaml"
+
+    args = argparse.Namespace(
+        repo_path=str(repo_path),
+        url=None,
+        override_name=None,
+        config=str(config_file),
+        workspace_root_path=None,
+        dry_run=False,
+        assume_yes=True,
+        merge_duplicates=True,
+    )
+
+    handle_add_command(args)
+
+    expected_label = "~/study/python/"
+    assert expected_label in caplog.text
+
+    import yaml
+
+    with config_file.open(encoding="utf-8") as fh:
+        config_data = yaml.safe_load(fh)
+
+    assert expected_label in config_data