diff --git a/agent/agentcontext/api_test.go b/agent/agentcontext/api_test.go
index 1563345d9e3e8..2a5abd2362396 100644
--- a/agent/agentcontext/api_test.go
+++ b/agent/agentcontext/api_test.go
@@ -61,7 +61,7 @@ func TestAPI_ListSourcesEmpty(t *testing.T) {
 func TestAPI_AddAndListSource(t *testing.T) {
 	t.Parallel()
 	wd := t.TempDir()
-	src := t.TempDir()
+	src := testutil.TempDirResolved(t)
 
 	srv, _ := newAPITestServer(t, agentcontext.ManagerOptions{
 		WorkingDir:   func() string { return wd },
@@ -103,7 +103,7 @@ func TestAPI_AddSourceRejected(t *testing.T) {
 func TestAPI_GetAndDeleteSource(t *testing.T) {
 	t.Parallel()
 	wd := t.TempDir()
-	src := t.TempDir()
+	src := testutil.TempDirResolved(t)
 
 	srv, m := newAPITestServer(t, agentcontext.ManagerOptions{
 		WorkingDir:   func() string { return wd },
diff --git a/agent/agentcontext/manager_test.go b/agent/agentcontext/manager_test.go
index 42a1edab03c8e..16ba6c4941353 100644
--- a/agent/agentcontext/manager_test.go
+++ b/agent/agentcontext/manager_test.go
@@ -67,8 +67,8 @@ func TestManager_InitialSnapshotIsPopulated(t *testing.T) {
 
 func TestManager_AddSourceTriggersResolve(t *testing.T) {
 	t.Parallel()
-	wd := t.TempDir()
-	src := t.TempDir()
+	wd := testutil.TempDirResolved(t)
+	src := testutil.TempDirResolved(t)
 	mustWriteFile(t, filepath.Join(src, "AGENTS.md"), "from source")
 
 	m := newTestManager(t, agentcontext.ManagerOptions{
@@ -194,7 +194,7 @@ func TestManager_RemoveSource(t *testing.T) {
 func TestManager_HasSource(t *testing.T) {
 	t.Parallel()
 	wd := t.TempDir()
-	src := t.TempDir()
+	src := testutil.TempDirResolved(t)
 
 	m := newTestManager(t, agentcontext.ManagerOptions{
 		WorkingDir:   func() string { return wd },
@@ -285,7 +285,7 @@ func TestManager_ResyncCanceledKeepsLiveSnapshot(t *testing.T) {
 func TestManager_InitialSourcesSeeded(t *testing.T) {
 	t.Parallel()
 	wd := t.TempDir()
-	src := t.TempDir()
+	src := testutil.TempDirResolved(t)
 	mustWriteFile(t, filepath.Join(src, "AGENTS.md"), "from initial")
 
 	m := newTestManager(t, agentcontext.ManagerOptions{
@@ -312,7 +312,7 @@ func TestManager_InitialSourcesSeeded(t *testing.T) {
 func TestManager_SeedSourcesLateBindsAfterManifest(t *testing.T) {
 	t.Parallel()
 	wd := t.TempDir()
-	late := t.TempDir()
+	late := testutil.TempDirResolved(t)
 	mustWriteFile(t, filepath.Join(late, "AGENTS.md"), "late binding")
 
 	// AllowedRoots intentionally omits `late` so AddSource
diff --git a/agent/agentcontext/paths_test.go b/agent/agentcontext/paths_test.go
index f70af76788140..c737bb338dcc2 100644
--- a/agent/agentcontext/paths_test.go
+++ b/agent/agentcontext/paths_test.go
@@ -10,6 +10,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/v2/agent/agentcontext"
+	"github.com/coder/coder/v2/testutil"
 )
 
 // switchHomeEnv overrides the platform-specific environment
@@ -99,7 +100,7 @@ func TestValidateSourcePath_RejectsParentSegments(t *testing.T) {
 
 func TestValidateSourcePath_AllowsInsideRoot(t *testing.T) {
 	t.Parallel()
-	dir := t.TempDir()
+	dir := testutil.TempDirResolved(t)
 	child := filepath.Join(dir, "child")
 	require.NoError(t, os.MkdirAll(child, 0o755))
 
diff --git a/agent/agentcontext/resolve.go b/agent/agentcontext/resolve.go
index 5f2dba9cf80eb..08a0fbe46f797 100644
--- a/agent/agentcontext/resolve.go
+++ b/agent/agentcontext/resolve.go
@@ -368,7 +368,16 @@ func resolveReadTarget(path string, info fs.FileInfo, scanRoot string) (readPath
 	if err != nil {
 		return "", nil, false, StatusUnreadable, fmt.Sprintf("symlink resolve: %v", err)
 	}
+	// Canonicalize scanRoot symmetrically with the target so the
+	// boundary check survives platform-level symlinks in the scan
+	// root prefix. macOS, for example, exposes /var as a symlink
+	// to /private/var; EvalSymlinks on the target produces a
+	// /private/var path while the caller's scanRoot may still be
+	// /var, which would incorrectly trip the prefix check.
 	rootClean := filepath.Clean(scanRoot)
+	if resolved, err := filepath.EvalSymlinks(rootClean); err == nil {
+		rootClean = resolved
+	}
 	if !pathHasPrefix(target, rootClean) {
 		return "", nil, false, StatusInvalid, fmt.Sprintf("symlink target %q escapes scan root %q", target, scanRoot)
 	}