diff --git a/internal/exec/adapter.go b/internal/exec/adapter.go
index 7a70610..7114e3d 100644
--- a/internal/exec/adapter.go
+++ b/internal/exec/adapter.go
@@ -3,12 +3,20 @@
 // merges stderr into stdout; the adapter preserves that contract.
 package exec
 
-import "context"
+import (
+	"context"
+	"strings"
+)
 
-// SessionAdapter is the bridge *Session → wire.Executer. The
-// `target` argument is accepted to match the forward-compatible
-// Executer signature; on 1.4a the shell does its own cwd
-// handling so target is dropped on the floor.
+// SessionAdapter is the bridge *Session → wire.Executer.
+//
+// The `target` argument is the validated, symlink-resolved working
+// directory the caller intended the command to run in. When
+// non-empty, the adapter prepends an explicit "cd <target>" to
+// the command so it executes in that directory regardless of the
+// bash session's current state. When empty, the command runs in
+// whatever cwd the shell's previous command left behind (backward-
+// compatible behaviour).
 type SessionAdapter struct {
 	S *Session
 }
@@ -19,9 +27,19 @@ func NewSessionAdapter(s *Session) *SessionAdapter {
 	return &SessionAdapter{S: s}
 }
 
-// Run forwards to the underlying session. See SessionAdapter
-// for the target-discard rationale.
-func (a *SessionAdapter) Run(ctx context.Context, _, cmd string) (string, string, int, error) {
+// shellQuote wraps s in single quotes, escaping any embedded
+// single quotes per POSIX convention.
+func shellQuote(s string) string {
+	return "'" + strings.ReplaceAll(s, "'", "'\\''") + "'"
+}
+
+// Run forwards to the underlying session, prepending an explicit
+// `cd <target>` when target is non-empty so the command executes
+// in the directory the caller asked for.
+func (a *SessionAdapter) Run(ctx context.Context, target, cmd string) (string, string, int, error) {
+	if target != "" {
+		cmd = "cd " + shellQuote(target) + "\n" + cmd
+	}
 	return a.S.Run(ctx, cmd)
 }
 
diff --git a/internal/wire/handler_exec.go b/internal/wire/handler_exec.go
index b668a9c..bddbf1d 100644
--- a/internal/wire/handler_exec.go
+++ b/internal/wire/handler_exec.go
@@ -246,7 +246,7 @@ func (h *ExecHandler) Handle(ctx context.Context, requestID string, payload map[
 	// ignored. The protocol field is preserved in the decoded
 	// payload so the upgrade is mechanical.
 	start := h.now()
-	stdout, stderr, exit, runErr := h.Shell.Run(callCtx, cwd, p.Command)
+	stdout, stderr, exit, runErr := h.Shell.Run(callCtx, canonical, p.Command)
 	duration := h.now().Sub(start)
 
 	// Prepend auto-cd warning to stderr if the cwd was outside
diff --git a/internal/wire/handler_fs.go b/internal/wire/handler_fs.go
index c3069fe..a5795e0 100644
--- a/internal/wire/handler_fs.go
+++ b/internal/wire/handler_fs.go
@@ -194,7 +194,11 @@ func (fsys *FileSystem) ReadHandler(ctx context.Context, requestID string, paylo
 	// Stat before reading. We want a distinct file_not_found
 	// error so the server can decide whether to retry (network
 	// mount slow to converge) or surface to the operator.
-	info, err := fsys.IO.Stat(p.Path)
+	// Use the canonical (symlink-resolved) path — NOT the raw
+	// p.Path — to close the TOCTOU window where a symlink
+	// swap between checkAllowed and Stat would bypass the
+	// allowlist.
+	info, err := fsys.IO.Stat(canonical)
 	if err != nil {
 		if errors.Is(err, fs.ErrNotExist) {
 			fsys.audit("read", canonical, "error", 0)
@@ -220,7 +224,7 @@ func (fsys *FileSystem) ReadHandler(ctx context.Context, requestID string, paylo
 		}), nil
 	}
 
-	data, err := fsys.IO.ReadFile(p.Path)
+	data, err := fsys.IO.ReadFile(canonical)
 	if err != nil {
 		fsys.audit("read", canonical, "error", 0)
 		return NewReadResultEnvelope(requestID, ReadResultPayload{
@@ -337,7 +341,7 @@ func (fsys *FileSystem) WriteHandler(ctx context.Context, requestID string, payl
 	// create a directory tree — a write to a non-existent
 	// parent returns ENOENT and surfaces as io_error.
 	const filePerm os.FileMode = 0o644
-	n, err := fsys.IO.WriteFile(p.Path, data, filePerm, mode)
+	n, err := fsys.IO.WriteFile(canonical, data, filePerm, mode)
 	if err != nil {
 		fsys.audit("write", canonical, "error", int64(0))
 		errCode := "io_error"