diff --git a/crates/tinytools-std/src/filesystem/file_write/mod.rs b/crates/tinytools-std/src/filesystem/file_write/mod.rs
index 0efcd66..25186d8 100644
--- a/crates/tinytools-std/src/filesystem/file_write/mod.rs
+++ b/crates/tinytools-std/src/filesystem/file_write/mod.rs
@@ -92,8 +92,10 @@ impl Tool for FileWriteTool {
     /// an external process to win the race — outside this gate's threat model,
     /// which governs the agent, not concurrent writers — and `execute()` still
     /// enforces workspace containment + symlink refusal regardless, so a write
-    /// that slips through as "create" cannot escape the sandbox. We therefore
-    /// do not re-probe in `execute()`.
+    /// that slips through as "create" cannot escape the sandbox. `execute()`
+    /// does re-probe for one case: a context workspace can resolve the path
+    /// somewhere other than this probe's root, and an existing file there that
+    /// this probe saw as new is refused rather than overwritten unapproved.
     fn external_effect_with_args(&self, args: &serde_json::Value) -> bool {
         if !self.gate.write_needs_approval() {
             return false; // Full (allow) or read-only (blocked in execute)
@@ -173,6 +175,20 @@ impl FileWriteTool {
             Err(msg) => return Ok(ToolResult::error(msg)),
         };
 
+        // Re-probe: the approval probe resolved `path` against the approval
+        // root, but a context workspace can move the write elsewhere. A path it
+        // saw as new (no approval asked) that exists here would be an
+        // unapproved overwrite.
+        if self.gate.write_needs_approval()
+            && !self.external_effect_with_args(&args)
+            && tokio::fs::symlink_metadata(&resolved_target).await.is_ok()
+        {
+            return Ok(ToolResult::error(format!(
+                "{path} already exists in this workspace; overwriting it needs approval. \
+                 Use the edit tool to change it"
+            )));
+        }
+
         // Create parent directory only at the validated, resolved location.
         if let Some(resolved_parent) = resolved_target.parent() {
             tokio::fs::create_dir_all(resolved_parent).await?;
diff --git a/crates/tinytools-std/src/filesystem/file_write/mod_tests.rs b/crates/tinytools-std/src/filesystem/file_write/mod_tests.rs
index 73407b3..e8946bb 100644
--- a/crates/tinytools-std/src/filesystem/file_write/mod_tests.rs
+++ b/crates/tinytools-std/src/filesystem/file_write/mod_tests.rs
@@ -500,3 +500,28 @@ async fn file_write_uses_the_context_workspace_when_one_is_threaded() {
     assert!(isolated.path().join("in_ws.txt").exists());
     assert!(!home.path().join("in_ws.txt").exists());
 }
+
+// The approval probe ran against the tool's approval root, where the path is
+// new, so no approval was asked. Under a context workspace the same path is an
+// existing file: overwriting it would be an unapproved edit.
+#[tokio::test]
+async fn an_overwrite_the_approval_probe_saw_as_a_create_is_refused() {
+    use crate::filesystem::test_support::WorkspaceContext;
+    let home = tempfile::tempdir().unwrap();
+    let isolated = tempfile::tempdir().unwrap();
+    std::fs::write(isolated.path().join("a.txt"), "keep").unwrap();
+    let tool = FileWriteTool::new(test_security(home.path().to_path_buf()));
+    let args = json!({"path": "a.txt", "content": "clobbered"});
+    assert!(!tool.external_effect_with_args(&args), "probed as a create");
+
+    let context = WorkspaceContext::at(isolated.path());
+    let result = tool
+        .execute_with_context(args, ToolCallOptions::default(), Some(&context))
+        .await
+        .unwrap();
+    assert!(result.is_error, "{}", result.output());
+    assert_eq!(
+        std::fs::read_to_string(isolated.path().join("a.txt")).unwrap(),
+        "keep"
+    );
+}