diff --git a/src-tauri/src/pty.rs b/src-tauri/src/pty.rs
index d4d78e5..13cb343 100644
--- a/src-tauri/src/pty.rs
+++ b/src-tauri/src/pty.rs
@@ -354,6 +354,23 @@ fn build_command(spec: &SpawnSpec) -> Result<(CommandBuilder, &'static str)> {
             let resolved_cwd = cwd.as_deref().unwrap_or("~");
             c.arg("--cd");
             c.arg(resolved_cwd);
+            // Make the shell report its working directory via OSC 7 on every
+            // prompt, so the frontend can map this pane to the claude session
+            // running in it (the context-fill indicator; see usage.rs +
+            // LeafPane). We set PROMPT_COMMAND in the environment and forward it
+            // through WSLENV — default Ubuntu bash inherits an env-provided
+            // PROMPT_COMMAND. A user shell that hard-assigns PROMPT_COMMAND (or
+            // a non-bash login shell) simply won't report, and the indicator
+            // stays hidden for that pane — no breakage either way.
+            c.env(
+                "PROMPT_COMMAND",
+                r#"printf '\033]7;file://%s%s\033\\' "$HOSTNAME" "$PWD""#,
+            );
+            let wslenv = match std::env::var("WSLENV") {
+                Ok(v) if !v.is_empty() => format!("{v}:PROMPT_COMMAND/u"),
+                _ => "PROMPT_COMMAND/u".to_string(),
+            };
+            c.env("WSLENV", wslenv);
             Ok((c, "failed to spawn wsl.exe; is WSL installed?"))
         }
         SpawnSpec::Powershell => {
diff --git a/src/components/XtermPane.tsx b/src/components/XtermPane.tsx
index a993c11..3ebb2a9 100644
--- a/src/components/XtermPane.tsx
+++ b/src/components/XtermPane.tsx
@@ -82,6 +82,10 @@ interface XtermPaneProps {
    *  Defined as an optional callback so single-pane windows don't require
    *  wiring it up. */
   onNavigate?: (intent: NavigateIntent) => void;
+  /** Fired with the shell's reported working directory (from an OSC 7 escape,
+   *  which WSL panes emit via an injected PROMPT_COMMAND — see pty.rs). Used to
+   *  map the pane to the claude session running in it. */
+  onCwd?: (cwd: string) => void;
 }
 
 const DEFAULT_XTERM_FONT_SIZE = 13;
@@ -101,6 +105,7 @@ export default function XtermPane({
   focusTrigger = 0,
   fontSize,
   onNavigate,
+  onCwd,
 }: XtermPaneProps) {
   const containerRef = useRef<HTMLDivElement>(null);
   const termRef = useRef<Terminal | null>(null);
@@ -121,6 +126,7 @@ export default function XtermPane({
   const onDataReceivedRef = useRef(onDataReceived);
   const onFocusRef = useRef(onFocus);
   const onNavigateRef = useRef(onNavigate);
+  const onCwdRef = useRef(onCwd);
   // Stable ref for setSearchOpen so it can be called from inside the
   // attachCustomKeyEventHandler closure without the closure going stale.
   const setSearchOpenRef = useRef<(v: boolean) => void>(setSearchOpen);
@@ -131,6 +137,7 @@ export default function XtermPane({
   useEffect(() => { onDataReceivedRef.current = onDataReceived; }, [onDataReceived]);
   useEffect(() => { onFocusRef.current = onFocus; }, [onFocus]);
   useEffect(() => { onNavigateRef.current = onNavigate; }, [onNavigate]);
+  useEffect(() => { onCwdRef.current = onCwd; }, [onCwd]);
   useEffect(() => { setSearchOpenRef.current = setSearchOpen; }, [setSearchOpen]);
 
   // -------------------------------------------------------------------------
@@ -204,6 +211,24 @@ export default function XtermPane({
     searchAddonRef.current = search;
     term.loadAddon(search);
 
+    // OSC 7 (cwd reporting): WSL panes emit `\e]7;file://<host><path>\e\\` on
+    // every prompt (via the PROMPT_COMMAND we inject at spawn). Capture the
+    // path and report it up so the pane can be matched to its claude session.
+    // Registered before data flows so the first prompt's cwd is caught.
+    term.parser.registerOscHandler(7, (data) => {
+      const m = /^file:\/\/[^/]*(\/.*)$/.exec(data);
+      if (m) {
+        let path = m[1];
+        try {
+          path = decodeURIComponent(path);
+        } catch {
+          /* leave raw if it isn't valid percent-encoding */
+        }
+        onCwdRef.current?.(path);
+      }
+      return true;
+    });
+
     // Initial size — fit before asking the PTY for its dimensions.
     fit.fit();
 
diff --git a/src/lib/layout/LeafPane.tsx b/src/lib/layout/LeafPane.tsx
index a158396..7b7a764 100644
--- a/src/lib/layout/LeafPane.tsx
+++ b/src/lib/layout/LeafPane.tsx
@@ -179,6 +179,15 @@ export default function LeafPane({ leaf }: { leaf: LeafNode }) {
     return () => ro.disconnect();
   }, []);
 
+  // Live cwd reported by the shell via OSC 7 (WSL panes). Used to match this
+  // pane to the claude session running in it — more reliable than leaf.cwd,
+  // which is the (often unset) spawn cwd and doesn't follow `cd`.
+  const [liveCwd, setLiveCwd] = useState<string | null>(null);
+  const onPaneCwd = useCallback(
+    (cwd: string) => setLiveCwd((cur) => (cur === cwd ? cur : cwd)),
+    [],
+  );
+
   // ---- broadcast ---------------------------------------------------------
   const onTerminalInput = useCallback(
     (b64: string) => {
@@ -409,8 +418,11 @@ export default function LeafPane({ leaf }: { leaf: LeafNode }) {
     };
   })();
 
+  const matchCwd = liveCwd ?? leaf.cwd;
   const ctx =
-    leaf.shellKind === "wsl" && leaf.cwd ? orch.paneContext.get(leaf.cwd) : undefined;
+    leaf.shellKind === "wsl" && matchCwd
+      ? orch.paneContext.get(matchCwd)
+      : undefined;
 
   return (
     <div
@@ -629,6 +641,7 @@ export default function LeafPane({ leaf }: { leaf: LeafNode }) {
             onDataReceived={onDataReceived}
             onFocus={onXtermFocus}
             onNavigate={onPaneNavigate}
+            onCwd={onPaneCwd}
             focusTrigger={focusTrigger}
             fontSize={resolveFontSize(leaf.fontSizeOffset)}
           />