diff --git a/pkg/unshare/unshare_linux.go b/pkg/unshare/unshare_linux.go
index c352efce0a..a0e9cee215 100644
--- a/pkg/unshare/unshare_linux.go
+++ b/pkg/unshare/unshare_linux.go
@@ -1,3 +1,4 @@
+//go:build linux
 // +build linux
 
 package unshare
@@ -7,6 +8,7 @@ import (
 	"bytes"
 	"fmt"
 	"io"
+	"io/fs"
 	"os"
 	"os/exec"
 	"os/signal"
@@ -76,6 +78,26 @@ func getRootlessGID() int {
 	return os.Getegid()
 }
 
+func isSetID(path string, modeid fs.FileMode, capid capability.Cap) (bool, error) {
+	info, err := os.Stat(path)
+	if err != nil {
+		return false, err
+	}
+
+	mode := info.Mode()
+	if mode&modeid == modeid {
+		return true, nil
+	}
+	cap, err := capability.NewFile2(path)
+	if err != nil {
+		return false, err
+	}
+	if err := cap.Load(); err != nil {
+		return false, err
+	}
+	return cap.Get(capability.EFFECTIVE, capid), nil
+}
+
 func (c *Cmd) Start() error {
 	runtime.LockOSThread()
 	defer runtime.UnlockOSThread()
@@ -215,15 +237,26 @@ func (c *Cmd) Start() error {
 			gidmapSet := false
 			// Set the GID map.
 			if c.UseNewgidmap {
-				cmd := exec.Command("newgidmap", append([]string{pidString}, strings.Fields(strings.Replace(g.String(), "\n", " ", -1))...)...)
+				path, err := exec.LookPath("newgidmap")
+				if err != nil {
+					return errors.Wrapf(err, "error finding newgidmap")
+				}
+				cmd := exec.Command(path, append([]string{pidString}, strings.Fields(strings.Replace(g.String(), "\n", " ", -1))...)...)
 				g.Reset()
 				cmd.Stdout = g
 				cmd.Stderr = g
-				err := cmd.Run()
-				if err == nil {
+				if err := cmd.Run(); err == nil {
 					gidmapSet = true
 				} else {
 					logrus.Warnf("Error running newgidmap: %v: %s", err, g.String())
+					isSetgid, err := isSetID(path, os.ModeSetgid, capability.CAP_SETGID)
+					if err != nil {
+						logrus.Warnf("Failed to check for setgid on %s: %v", path, err)
+					} else {
+						if !isSetgid {
+							logrus.Warnf("%s should be setgid or have filecaps setgid", path)
+						}
+					}
 					logrus.Warnf("Falling back to single mapping")
 					g.Reset()
 					g.Write([]byte(fmt.Sprintf("0 %d 1\n", os.Getegid())))
@@ -262,17 +295,29 @@ func (c *Cmd) Start() error {
 				fmt.Fprintf(u, "%d %d %d\n", m.ContainerID, m.HostID, m.Size)
 			}
 			uidmapSet := false
-			// Set the GID map.
+			// Set the UID map.
 			if c.UseNewuidmap {
-				cmd := exec.Command("newuidmap", append([]string{pidString}, strings.Fields(strings.Replace(u.String(), "\n", " ", -1))...)...)
+				path, err := exec.LookPath("newuidmap")
+				if err != nil {
+					return errors.Wrapf(err, "error finding newuidmap")
+				}
+				cmd := exec.Command(path, append([]string{pidString}, strings.Fields(strings.Replace(u.String(), "\n", " ", -1))...)...)
 				u.Reset()
 				cmd.Stdout = u
 				cmd.Stderr = u
-				err := cmd.Run()
-				if err == nil {
+				if err := cmd.Run(); err == nil {
 					uidmapSet = true
 				} else {
 					logrus.Warnf("Error running newuidmap: %v: %s", err, u.String())
+					isSetuid, err := isSetID(path, os.ModeSetuid, capability.CAP_SETUID)
+					if err != nil {
+						logrus.Warnf("Failed to check for setuid on %s: %v", path, err)
+					} else {
+						if !isSetuid {
+							logrus.Warnf("%s should be setuid or have filecaps setuid", path)
+						}
+					}
+
 					logrus.Warnf("Falling back to single mapping")
 					u.Reset()
 					u.Write([]byte(fmt.Sprintf("0 %d 1\n", os.Geteuid())))