diff --git a/cmd/internal/agentworkspace/up.go b/cmd/internal/agentworkspace/up.go
index 28ed2a1b5..d52e2680e 100644
--- a/cmd/internal/agentworkspace/up.go
+++ b/cmd/internal/agentworkspace/up.go
@@ -544,7 +544,6 @@ func prepareWorkspace(params prepareWorkspaceParams) error {
 		params.workspaceInfo.Workspace.Source.LocalFolder != "" {
 		params.workspaceInfo.ContentFolder = agent.GetAgentWorkspaceContentDir(
 			params.workspaceInfo.Origin,
-			params.workspaceInfo.Workspace.UID,
 		)
 	}
 
diff --git a/pkg/agent/agent.go b/pkg/agent/agent.go
index 85fda2fce..49f824a06 100644
--- a/pkg/agent/agent.go
+++ b/pkg/agent/agent.go
@@ -246,7 +246,7 @@ func handleStaleWorkspace(
 		return "", fmt.Errorf("recreate workspace dir: %w", err)
 	}
 
-	// Drop the old UID's path so resolveContentFolder picks up the new one.
+	// Clear so resolveContentFolder recomputes against the recreated dir.
 	workspaceInfo.ContentFolder = ""
 	return newDir, nil
 }
@@ -264,12 +264,23 @@ func resolveContentFolder(
 			workspaceInfo.ContentFolder = workspaceInfo.Workspace.Source.LocalFolder
 		}
 	}
-	if workspaceInfo.ContentFolder == "" {
-		workspaceInfo.ContentFolder = GetAgentWorkspaceContentDir(
-			workspaceDir,
-			workspaceInfo.Workspace.UID,
-		)
+	if workspaceInfo.ContentFolder != "" {
+		return
+	}
+
+	// On the host, place the bind-mount source under the delete-stable
+	// "contents" dir so its parent inode survives up -> delete -> up.
+	if IsHostAgentInvocation(workspaceInfo.Agent.DataPath) {
+		if contentDir, err := provider2.GetWorkspaceContentDir(
+			workspaceInfo.Workspace.Context,
+			workspaceInfo.Workspace.ID,
+		); err == nil {
+			workspaceInfo.ContentFolder = contentDir
+			return
+		}
 	}
+
+	workspaceInfo.ContentFolder = GetAgentWorkspaceContentDir(workspaceDir)
 }
 
 func CreateWorkspaceBusyFile(folder string) {
diff --git a/pkg/agent/workspace.go b/pkg/agent/workspace.go
index 5b4ba88e0..38e241786 100644
--- a/pkg/agent/workspace.go
+++ b/pkg/agent/workspace.go
@@ -215,11 +215,8 @@ echo Devsy
 	return true, nil
 }
 
-// GetAgentWorkspaceContentDir returns the bind-mount source for a workspace.
-// The UID suffix ensures a delete-then-recreate cycle never reuses the same
-// host path, avoiding Docker Desktop's stale /host_mnt inode cache.
-func GetAgentWorkspaceContentDir(workspaceDir, uid string) string {
-	return filepath.Join(workspaceDir, "content-"+uid)
+func GetAgentWorkspaceContentDir(workspaceDir string) string {
+	return filepath.Join(workspaceDir, "content")
 }
 
 func GetAgentBinariesDirFromWorkspaceDir(workspaceDir string) (string, error) {
diff --git a/pkg/client/clientimplementation/workspace_client.go b/pkg/client/clientimplementation/workspace_client.go
index c19064f77..8ae274df9 100644
--- a/pkg/client/clientimplementation/workspace_client.go
+++ b/pkg/client/clientimplementation/workspace_client.go
@@ -870,6 +870,15 @@ func DeleteWorkspaceFolder(params DeleteWorkspaceFolderParams) error {
 		return err
 	}
 
+	// remove the content folder leaf (outside WorkspaceDir); leave its parent
+	// "contents" dir in place to keep its host inode stable across recreate.
+	contentFolder, err := provider.GetWorkspaceContentDir(params.Context, params.WorkspaceID)
+	if err == nil {
+		if err := os.RemoveAll(contentFolder); err != nil && !os.IsNotExist(err) {
+			return err
+		}
+	}
+
 	return nil
 }
 
diff --git a/pkg/config/pathmanager.go b/pkg/config/pathmanager.go
index dead55942..006f702be 100644
--- a/pkg/config/pathmanager.go
+++ b/pkg/config/pathmanager.go
@@ -41,6 +41,8 @@ type PathManager interface {
 	WorkspacesDir(context string) (string, error)
 	WorkspaceDir(context, workspaceID string) (string, error)
 	WorkspaceAgentDir(context, workspaceID string) (string, error)
+	WorkspaceContentsDir(context string) (string, error)
+	WorkspaceContentDir(context, workspaceID string) (string, error)
 	WorkspaceLogDir(context, workspaceID string) (string, error)
 	MachinesDir(context string) (string, error)
 	MachineDir(context, machineID string) (string, error)
@@ -135,6 +137,29 @@ func (b *basePathManager) WorkspaceAgentDir(context, workspaceID string) (string
 	return filepath.Join(dir, "agent"), nil
 }
 
+// WorkspaceContentsDir is the per-context parent of workspace content folders.
+// It is never removed on delete, keeping a stable host inode for the bind-mount
+// source's parent across up -> delete -> up (avoids Docker Desktop's stale
+// file-share inode cache).
+func (b *basePathManager) WorkspaceContentsDir(context string) (string, error) {
+	dir, err := b.ContextDir(context)
+	if err != nil {
+		return "", err
+	}
+
+	return filepath.Join(dir, "contents"), nil
+}
+
+// WorkspaceContentDir is the bind-mount source leaf under WorkspaceContentsDir.
+func (b *basePathManager) WorkspaceContentDir(context, workspaceID string) (string, error) {
+	dir, err := b.WorkspaceContentsDir(context)
+	if err != nil {
+		return "", err
+	}
+
+	return filepath.Join(dir, workspaceID), nil
+}
+
 // WorkspaceLogDir is the per-workspace log directory used by the desktop's
 // streaming-log store. Lives under WorkspaceDir for the same reason as
 // WorkspaceAgentDir.
diff --git a/pkg/config/pathmanager_linux_test.go b/pkg/config/pathmanager_linux_test.go
index 8ff235506..58d0b0455 100644
--- a/pkg/config/pathmanager_linux_test.go
+++ b/pkg/config/pathmanager_linux_test.go
@@ -131,6 +131,16 @@ func TestContextDataSubPaths(t *testing.T) {
 			func() (string, error) { return pm.WorkspaceAgentDir(ctx, "ws1") },
 			filepath.Join(base, "workspaces", "ws1", "agent"),
 		},
+		{
+			"WorkspaceContentsDir",
+			func() (string, error) { return pm.WorkspaceContentsDir(ctx) },
+			filepath.Join(base, "contents"),
+		},
+		{
+			"WorkspaceContentDir",
+			func() (string, error) { return pm.WorkspaceContentDir(ctx, "ws1") },
+			filepath.Join(base, "contents", "ws1"),
+		},
 		{
 			"WorkspaceLogDir",
 			func() (string, error) { return pm.WorkspaceLogDir(ctx, "ws1") },
diff --git a/pkg/docker/helper.go b/pkg/docker/helper.go
index e72c3a020..1cc34a30d 100644
--- a/pkg/docker/helper.go
+++ b/pkg/docker/helper.go
@@ -75,6 +75,17 @@ func (r *DockerHelper) GetRuntime() ContainerRuntime {
 	return DetectRuntime(r.DockerCommand)
 }
 
+// ClientVersion returns the docker CLI version (e.g. "29.5.3"), or "".
+func (r *DockerHelper) ClientVersion(ctx context.Context) string {
+	cctx, cancel := context.WithTimeout(ctx, 5*time.Second)
+	defer cancel()
+	out, err := r.buildCmd(cctx, "version", "--format", "{{.Client.Version}}").Output()
+	if err != nil {
+		return ""
+	}
+	return strings.TrimSpace(string(out))
+}
+
 func (r *DockerHelper) FindDevContainer(
 	ctx context.Context,
 	labels []string,
diff --git a/pkg/driver/docker/docker.go b/pkg/driver/docker/docker.go
index 5526b2fe6..f83360472 100644
--- a/pkg/driver/docker/docker.go
+++ b/pkg/driver/docker/docker.go
@@ -660,11 +660,65 @@ func (d *dockerDriver) addWorkspaceMountArgs(
 		if !helper.GetRuntime().SupportsMountConsistency() {
 			mountPath = stripMountConsistency(mountPath)
 		}
+		if shouldBustBindCache(helper) {
+			mountPath = withBindCreateSrc(mountPath)
+		}
 		args = append(args, "--mount", mountPath)
 	}
 	return args
 }
 
+// minBindCreateSrcMajor is the docker CLI major version that added the
+// bind-create-src mount option; older clients reject it at parse time.
+const minBindCreateSrcMajor = 29
+
+// shouldBustBindCache reports whether to add bind-create-src to the workspace
+// mount. Gated to Docker (Podman/nerdctl reject it), Docker Desktop
+// (GOOS != linux), and CLI >= v29.
+func shouldBustBindCache(helper *docker.DockerHelper) bool {
+	if helper.GetRuntime().Name() != docker.RuntimeDocker {
+		return false
+	}
+	if runtime.GOOS == "linux" {
+		return false
+	}
+	return dockerMajorAtLeast(helper.ClientVersion(context.Background()), minBindCreateSrcMajor)
+}
+
+// dockerMajorAtLeast reports whether version's major component is >= minMajor.
+// An unparseable version returns false.
+func dockerMajorAtLeast(version string, minMajor int) bool {
+	major, _, ok := strings.Cut(version, ".")
+	if !ok {
+		return false
+	}
+	n, err := strconv.Atoi(strings.TrimSpace(major))
+	if err != nil {
+		return false
+	}
+	return n >= minMajor
+}
+
+// withBindCreateSrc adds bind-create-src=true to a bind --mount whose source
+// exists, forcing Docker Desktop to re-resolve a stale-cached path. A missing
+// source is left untouched so docker still fails loudly rather than binding an
+// empty dir.
+func withBindCreateSrc(mountPath string) string {
+	m := config.ParseMount(mountPath)
+	if m.Type != "bind" || m.Source == "" {
+		return mountPath
+	}
+	for part := range strings.SplitSeq(mountPath, ",") {
+		if strings.HasPrefix(part, "bind-create-src=") {
+			return mountPath
+		}
+	}
+	if _, err := os.Stat(m.Source); err != nil {
+		return mountPath
+	}
+	return mountPath + ",bind-create-src=true"
+}
+
 func stripMountConsistency(mount string) string {
 	var parts []string
 	for part := range strings.SplitSeq(mount, ",") {
diff --git a/pkg/driver/docker/docker_test.go b/pkg/driver/docker/docker_test.go
index 89d2d6003..73a449d1b 100644
--- a/pkg/driver/docker/docker_test.go
+++ b/pkg/driver/docker/docker_test.go
@@ -265,6 +265,44 @@ func (s *DockerDriverTestSuite) TestStripMountConsistency() {
 	}
 }
 
+func (s *DockerDriverTestSuite) TestWithBindCreateSrc() {
+	existing := s.T().TempDir()
+
+	// source exists -> option appended
+	withExisting := "type=bind,src=" + existing + ",dst=/b"
+	s.Equal(withExisting+",bind-create-src=true", withBindCreateSrc(withExisting))
+
+	// source missing -> untouched
+	s.Equal(testBindMount, withBindCreateSrc(testBindMount))
+
+	// idempotent
+	already := withExisting + ",bind-create-src=true"
+	s.Equal(already, withBindCreateSrc(already))
+
+	// non-bind ignored
+	vol := "type=volume,src=myvol,dst=/b"
+	s.Equal(vol, withBindCreateSrc(vol))
+}
+
+func (s *DockerDriverTestSuite) TestDockerMajorAtLeast() {
+	tests := []struct {
+		version string
+		want    bool
+	}{
+		{"29.5.3", true},
+		{"29.0.0", true},
+		{"30.1.0", true},
+		{"28.0.4", false},
+		{"20.10.21", false},
+		{"", false},
+		{"garbage", false},
+	}
+	for _, tt := range tests {
+		s.Equalf(tt.want, dockerMajorAtLeast(tt.version, minBindCreateSrcMajor),
+			"dockerMajorAtLeast(%q)", tt.version)
+	}
+}
+
 func (s *DockerDriverTestSuite) TestAddRunPlatform_SetAppendsFlag() {
 	b := &runArgsBuilder{
 		args:   []string{testRunArg},
diff --git a/pkg/provider/dir.go b/pkg/provider/dir.go
index c42fa46cd..c5e5fd2b3 100644
--- a/pkg/provider/dir.go
+++ b/pkg/provider/dir.go
@@ -85,6 +85,22 @@ func GetWorkspaceAgentDir(context, workspaceID string) (string, error) {
 	return config.DefaultPathManager().WorkspaceAgentDir(context, workspaceID)
 }
 
+// GetWorkspaceContentsDir returns the per-context parent of workspace content
+// folders (.../contexts/<ctx>/contents).
+func GetWorkspaceContentsDir(context string) (string, error) {
+	return config.DefaultPathManager().WorkspaceContentsDir(context)
+}
+
+// GetWorkspaceContentDir returns the host-side bind-mount source for a
+// workspace (.../contexts/<ctx>/contents/<id>).
+func GetWorkspaceContentDir(context, workspaceID string) (string, error) {
+	if workspaceID == "" {
+		return "", fmt.Errorf("workspace id is empty")
+	}
+
+	return config.DefaultPathManager().WorkspaceContentDir(context, workspaceID)
+}
+
 // GetWorkspaceLogDir returns the per-workspace log dir
 // (.../workspaces/<id>/logs) used by the desktop's streaming-log store.
 func GetWorkspaceLogDir(context, workspaceID string) (string, error) {