diff --git a/internal/shim/manager/manager_unix.go b/internal/shim/manager/manager_unix.go
index 7f9848e..1512be0 100644
--- a/internal/shim/manager/manager_unix.go
+++ b/internal/shim/manager/manager_unix.go
@@ -186,10 +186,32 @@ func (manager) Start(ctx context.Context, bparams *bootapi.BootstrapParams) (_ *
 		cmd.ExtraFiles = append(cmd.ExtraFiles, s.f)
 	}
 
-	cloneMntNs(ctx, cmd)
+	userns := cloneMntNs(ctx, cmd)
 
-	if err := cmd.Start(); err != nil {
-		return nil, err
+	if startErr := cmd.Start(); startErr != nil {
+		if !userns {
+			return nil, startErr
+		}
+		// clone(CLONE_NEWUSER) can fail for reasons not covered by the
+		// proactive AppArmor check — e.g. seccomp filters, LSM policies,
+		// or EACCES from the child's capability recomputation when
+		// inherited socket fds cross the user namespace boundary after
+		// exec. Retry without namespace isolation rather than failing
+		// the container start.
+		//
+		// Note: we cannot log here — during "start" the logger output
+		// goes to stderr which containerd captures as part of the
+		// bootstrap response (CombinedOutput), corrupting the JSON.
+		cmd, err = newCommand(ctx, id, bparams.ContainerdGrpcAddress, bparams.ContainerdTtrpcAddress, debug)
+		if err != nil {
+			return nil, err
+		}
+		for _, s := range sockets {
+			cmd.ExtraFiles = append(cmd.ExtraFiles, s.f)
+		}
+		if err := cmd.Start(); err != nil {
+			return nil, fmt.Errorf("retry without userns failed: %w (original error: %v)", err, startErr)
+		}
 	}
 
 	defer func() {
diff --git a/internal/shim/manager/mount_linux.go b/internal/shim/manager/mount_linux.go
index c7f2191..d19b9b1 100644
--- a/internal/shim/manager/mount_linux.go
+++ b/internal/shim/manager/mount_linux.go
@@ -52,19 +52,18 @@ import (
 // filesystem setup.
 //
 // If namespace creation is not possible (e.g. AppArmor restricts
-// unprivileged user namespaces), the function logs a warning and the shim
-// will run without mount isolation.
-func cloneMntNs(_ context.Context, cmd *exec.Cmd) {
+// unprivileged user namespaces), the shim runs without mount isolation
+// and this function returns false.
+// cloneMntNs returns true if user namespace clone flags were set.
+func cloneMntNs(_ context.Context, cmd *exec.Cmd) bool {
 	if restricted, err := apparmorRestrictsUserns(); err != nil {
 		// Failed to check apparmor userns restriction, skipping mount namespace isolation")
 		// We can't log anything here as it will break the TTRPC protocol!
-		// TODO(vvoland): Find a better way to surface this to the user.
-		return
+		return false
 	} else if restricted {
 		// apparmor_restrict_unprivileged_userns=1 prevents user namespace creation; shim will run without mount namespace isolation
 		// We can't log anything here as it will break the TTRPC protocol!
-		// TODO(vvoland): Find a better way to surface this to the user.
-		return
+		return false
 	}
 
 	uid := os.Getuid()
@@ -76,6 +75,7 @@ func cloneMntNs(_ context.Context, cmd *exec.Cmd) {
 	cmd.SysProcAttr.GidMappings = []syscall.SysProcIDMap{
 		{ContainerID: gid, HostID: gid, Size: 1},
 	}
+	return true
 }
 
 // apparmorRestrictsUserns checks if the kernel sysctl
diff --git a/internal/shim/manager/mount_other.go b/internal/shim/manager/mount_other.go
index 8adaa1b..30eccfa 100644
--- a/internal/shim/manager/mount_other.go
+++ b/internal/shim/manager/mount_other.go
@@ -23,4 +23,4 @@ import (
 	"os/exec"
 )
 
-func cloneMntNs(_ context.Context, _ *exec.Cmd) {}
+func cloneMntNs(_ context.Context, _ *exec.Cmd) bool { return false }