diff --git a/crates/socket-patch-cli/tests/hosted_memory_engine.rs b/crates/socket-patch-cli/tests/hosted_memory_engine.rs
index cc00ffc4f..af468e149 100644
--- a/crates/socket-patch-cli/tests/hosted_memory_engine.rs
+++ b/crates/socket-patch-cli/tests/hosted_memory_engine.rs
@@ -2281,7 +2281,9 @@ async fn user_patched_npm_packages_are_never_pinned() {
             .unwrap_or_else(|| panic!("{fixture} {file}: {:?}", project.skipped));
         assert_eq!(skip.purl, "pkg:npm/left-pad@1.3.0");
         assert!(
-            skip.detail.as_deref().is_some_and(|d| d.contains(file)),
+            skip.detail
+                .as_deref()
+                .is_some_and(|d| d.replace('\\', "/").contains(file)),
             "{fixture}: {:?}",
             skip.detail
         );
diff --git a/crates/socket-patch-core/src/patch/user_patches.rs b/crates/socket-patch-core/src/patch/user_patches.rs
index 5e17d12b9..700b05b2b 100644
--- a/crates/socket-patch-core/src/patch/user_patches.rs
+++ b/crates/socket-patch-core/src/patch/user_patches.rs
@@ -1232,7 +1232,12 @@ impl Bound {
                     )
             }
             Bound::Disk { root, repo } => {
-                !normalize_lexically_keeping_escapes(&root.join(rel)).starts_with(repo)
+                // `repo` is canonical (`\\?\C:\...` on Windows) while a
+                // script names a directory as users type it (`C:\...`), and
+                // `starts_with` treats the two prefixes as different.
+                use crate::utils::pnpm_workspace::without_verbatim_prefix;
+                !without_verbatim_prefix(normalize_lexically_keeping_escapes(&root.join(rel)))
+                    .starts_with(without_verbatim_prefix(repo.clone()))
             }
         }
     }
@@ -2058,14 +2063,14 @@ mod tests {
         assert!(
             left_pad
                 .iter()
-                .any(|s| s.ends_with("fixes/left-pad+1.3.0.patch")),
+                .any(|s| s.replace('\\', "/").ends_with("fixes/left-pad+1.3.0.patch")),
             "{left_pad:?}"
         );
         let is_number = global.conflicts("pkg:npm/is-number@7.0.0");
         assert!(
-            is_number
-                .iter()
-                .any(|s| s.ends_with("shared/a/patches/is-number+7.0.0.patch")),
+            is_number.iter().any(|s| s
+                .replace('\\', "/")
+                .ends_with("shared/a/patches/is-number+7.0.0.patch")),
             "{is_number:?}"
         );
         assert!(global.conflicts("pkg:npm/right-pad@1.3.0").is_empty());
@@ -2115,15 +2120,17 @@ mod tests {
         let tmp = tempfile::tempdir().unwrap();
         let repo = std::fs::canonicalize(tmp.path()).unwrap();
         write(&repo, ".git/HEAD", "ref: refs/heads/main\n");
-        let fixes = repo.join("fixes");
-        write(
-            &repo,
-            "package.json",
-            &format!(
-                r#"{{"scripts":{{"postinstall":"patch-package --patch-dir {}"}}}}"#,
-                fixes.display()
-            ),
-        );
+        // Spelled as a user types it: on Windows without the `\\?\` prefix
+        // `canonicalize` adds to `repo`, quoted in case the temp dir has a
+        // space, and built as JSON so its backslashes are escaped.
+        let fixes =
+            crate::utils::pnpm_workspace::without_verbatim_prefix(repo.clone()).join("fixes");
+        let manifest = serde_json::json!({
+            "scripts": {
+                "postinstall": format!("patch-package --patch-dir \"{}\"", fixes.display())
+            }
+        });
+        write(&repo, "package.json", &manifest.to_string());
         write(&repo, "fixes/left-pad+1.3.0.patch", "diff\n");
         let index = UserPatchIndex::discover(&repo).await;
         assert!(
diff --git a/crates/socket-patch-core/src/utils/cargo_build_cache.rs b/crates/socket-patch-core/src/utils/cargo_build_cache.rs
index 116888c1b..bcbd3bcab 100644
--- a/crates/socket-patch-core/src/utils/cargo_build_cache.rs
+++ b/crates/socket-patch-core/src/utils/cargo_build_cache.rs
@@ -437,7 +437,13 @@ mod tests {
         .unwrap();
         let warnings = invalidate_project(ReadScope::Workspace, &app, purls);
         assert_eq!(warnings.len(), 1, "{warnings:?}");
-        assert!(warnings[0].1.contains(".cargo/config.toml"), "{warnings:?}");
+        assert!(
+            warnings[0]
+                .1
+                .replace('\\', "/")
+                .contains(".cargo/config.toml"),
+            "{warnings:?}"
+        );
         // A global run reads it as before.
         assert!(invalidate_project(ReadScope::Global, &app, purls).is_empty());
     }
diff --git a/crates/socket-patch-core/src/utils/repo_root_upward_tests.rs b/crates/socket-patch-core/src/utils/repo_root_upward_tests.rs
index f7f22b82c..fc4571069 100644
--- a/crates/socket-patch-core/src/utils/repo_root_upward_tests.rs
+++ b/crates/socket-patch-core/src/utils/repo_root_upward_tests.rs
@@ -135,7 +135,8 @@ fn pnpm_workspace_file_above_the_repository_fails_closed() {
     write(&file, "packages:\n  - other\n");
     assert_eq!(
         crate::utils::pnpm_workspace::governing_workspace_file(&l.app),
-        Some(file)
+        // Reported without Windows' `\\?\` prefix, which `layout` keeps.
+        Some(crate::utils::pnpm_workspace::without_verbatim_prefix(file))
     );
     let plain = layout(false);
     write(
diff --git a/crates/socket-patch-core/src/vex/discover/user_patched.rs b/crates/socket-patch-core/src/vex/discover/user_patched.rs
index 7fd7fcede..7258c233d 100644
--- a/crates/socket-patch-core/src/vex/discover/user_patched.rs
+++ b/crates/socket-patch-core/src/vex/discover/user_patched.rs
@@ -328,6 +328,7 @@ mod tests {
             assert!(
                 out.unattested[0]
                     .detail
+                    .replace('\\', "/")
                     .contains("patches/left-pad+1.3.0.patch"),
                 "{}",
                 out.unattested[0].detail
@@ -420,7 +421,7 @@ mod tests {
             all_marked(&out, what);
             let member = files[files.len() - 1].0.rsplit_once('/').unwrap().0;
             assert!(
-                out.unattested[0].detail.contains(member),
+                out.unattested[0].detail.replace('\\', "/").contains(member),
                 "{what}: {}",
                 out.unattested[0].detail
             );