diff --git a/codex-rs/sandboxing/src/policy_transforms.rs b/codex-rs/sandboxing/src/policy_transforms.rs
index 134ac84f15..6d30b0f6f4 100644
--- a/codex-rs/sandboxing/src/policy_transforms.rs
+++ b/codex-rs/sandboxing/src/policy_transforms.rs
@@ -383,9 +383,15 @@ fn materialize_cwd_dependent_entry(
                 access: entry.access,
             })
             .unwrap_or_else(|| entry.clone()),
-        FileSystemPath::Path { .. }
-        | FileSystemPath::GlobPattern { .. }
-        | FileSystemPath::Special { .. } => entry.clone(),
+        FileSystemPath::GlobPattern { pattern } => FileSystemSandboxEntry {
+            path: FileSystemPath::GlobPattern {
+                pattern: AbsolutePathBuf::resolve_path_against_base(pattern, cwd)
+                    .to_string_lossy()
+                    .into_owned(),
+            },
+            access: entry.access,
+        },
+        FileSystemPath::Path { .. } | FileSystemPath::Special { .. } => entry.clone(),
     }
 }
 
diff --git a/codex-rs/sandboxing/src/policy_transforms_tests.rs b/codex-rs/sandboxing/src/policy_transforms_tests.rs
index e34158bc99..a0c93d9122 100644
--- a/codex-rs/sandboxing/src/policy_transforms_tests.rs
+++ b/codex-rs/sandboxing/src/policy_transforms_tests.rs
@@ -509,6 +509,75 @@ fn intersect_permission_profiles_rejects_concrete_grants_matched_by_requested_de
     );
 }
 
+#[test]
+fn intersect_permission_profiles_materializes_relative_deny_globs_for_reuse() {
+    let temp_dir = TempDir::new().expect("create temp dir");
+    let request_cwd = AbsolutePathBuf::from_absolute_path(temp_dir.path().join("request-cwd"))
+        .expect("absolute request cwd");
+    let later_cwd = AbsolutePathBuf::from_absolute_path(temp_dir.path().join("later-cwd"))
+        .expect("absolute later cwd");
+    let cwd_write = FileSystemSandboxEntry {
+        path: FileSystemPath::Special {
+            value: FileSystemSpecialPath::CurrentWorkingDirectory,
+        },
+        access: FileSystemAccessMode::Write,
+    };
+    let deny_env_files = FileSystemSandboxEntry {
+        path: FileSystemPath::GlobPattern {
+            pattern: "**/*.env".to_string(),
+        },
+        access: FileSystemAccessMode::None,
+    };
+    let permissions = PermissionProfile {
+        file_system: Some(FileSystemPermissions {
+            entries: vec![cwd_write, deny_env_files],
+            glob_scan_max_depth: std::num::NonZeroUsize::new(2),
+        }),
+        ..Default::default()
+    };
+
+    let intersected =
+        intersect_permission_profiles(permissions.clone(), permissions, request_cwd.as_path());
+
+    assert_eq!(
+        intersected,
+        PermissionProfile {
+            file_system: Some(FileSystemPermissions {
+                entries: vec![
+                    FileSystemSandboxEntry {
+                        path: FileSystemPath::Path {
+                            path: request_cwd.clone(),
+                        },
+                        access: FileSystemAccessMode::Write,
+                    },
+                    FileSystemSandboxEntry {
+                        path: FileSystemPath::GlobPattern {
+                            pattern: request_cwd.join("**/*.env").to_string_lossy().into_owned(),
+                        },
+                        access: FileSystemAccessMode::None,
+                    },
+                ],
+                glob_scan_max_depth: std::num::NonZeroUsize::new(2),
+            }),
+            ..Default::default()
+        }
+    );
+    assert_eq!(
+        intersect_permission_profiles(
+            PermissionProfile {
+                file_system: Some(FileSystemPermissions::from_read_write_roots(
+                    /*read*/ None,
+                    Some(vec![later_cwd.join("token.env")]),
+                )),
+                ..Default::default()
+            },
+            intersected,
+            later_cwd.as_path(),
+        ),
+        PermissionProfile::default()
+    );
+}
+
 #[test]
 fn intersect_permission_profiles_drops_broader_cwd_grant_for_requested_child_path() {
     let temp_dir = TempDir::new().expect("create temp dir");
@@ -577,7 +646,20 @@ fn intersect_permission_profiles_uses_granted_bounded_glob_scan_depth() {
         intersect_permission_profiles(requested, granted, cwd.as_path()),
         PermissionProfile {
             file_system: Some(FileSystemPermissions {
-                entries: vec![root_write, deny_env_files],
+                entries: vec![
+                    root_write,
+                    FileSystemSandboxEntry {
+                        path: FileSystemPath::GlobPattern {
+                            pattern: AbsolutePathBuf::resolve_path_against_base(
+                                "**/*.env",
+                                cwd.as_path()
+                            )
+                            .to_string_lossy()
+                            .into_owned(),
+                        },
+                        access: FileSystemAccessMode::None,
+                    },
+                ],
                 glob_scan_max_depth: std::num::NonZeroUsize::new(4),
             }),
             ..Default::default()
@@ -619,7 +701,20 @@ fn intersect_permission_profiles_uses_granted_unbounded_glob_scan_depth() {
         intersect_permission_profiles(requested, granted, cwd.as_path()),
         PermissionProfile {
             file_system: Some(FileSystemPermissions {
-                entries: vec![root_write, deny_env_files],
+                entries: vec![
+                    root_write,
+                    FileSystemSandboxEntry {
+                        path: FileSystemPath::GlobPattern {
+                            pattern: AbsolutePathBuf::resolve_path_against_base(
+                                "**/*.env",
+                                cwd.as_path()
+                            )
+                            .to_string_lossy()
+                            .into_owned(),
+                        },
+                        access: FileSystemAccessMode::None,
+                    },
+                ],
                 glob_scan_max_depth: None,
             }),
             ..Default::default()