diff --git a/src/cmd/create.go b/src/cmd/create.go
index f99342c..e3245b4 100644
--- a/src/cmd/create.go
+++ b/src/cmd/create.go
@@ -518,7 +518,11 @@ func getDBusSystemSocket() (string, error) {
 	path := addressSplit[1]
 	pathEvaled, err := filepath.EvalSymlinks(path)
 	if err != nil {
-		return "", fmt.Errorf("failed to resolve the path to the D-Bus system socket: %w", err)
+		logrus.Debugf("Resolving path to the D-Bus system socket: failed to evaluate symbolic links in %s: %s",
+			path,
+			err)
+
+		return "", errors.New("failed to resolve the path to the D-Bus system socket")
 	}
 
 	return pathEvaled, nil
@@ -586,7 +590,11 @@ func getServiceSocket(serviceName string, unitName string) (string, error) {
 
 	connection, err := dbus.SystemBus()
 	if err != nil {
-		return "", fmt.Errorf("failed to connect to the D-Bus system instance: %w", err)
+		logrus.Debugf("Resolving path to the %s socket: failed to connect to the D-Bus system instance: %s",
+			serviceName,
+			err)
+
+		return "", errors.New("failed to connect to the D-Bus system instance")
 	}
 
 	unitNameEscaped := systemdPathBusEscape(unitName)
@@ -597,7 +605,12 @@ func getServiceSocket(serviceName string, unitName string) (string, error) {
 	var result map[string]dbus.Variant
 	err = call.Store(&result)
 	if err != nil {
-		return "", fmt.Errorf("failed to get the properties of %s: %w", unitName, err)
+		logrus.Debugf("Resolving path to the %s socket: failed to get the properties of %s: %s",
+			serviceName,
+			unitName,
+			err)
+
+		return "", fmt.Errorf("failed to get the properties of %s", unitName)
 	}
 
 	listenVariant, listenFound := result["Listen"]
diff --git a/src/cmd/list.go b/src/cmd/list.go
index e9f676a..8893e5d 100644
--- a/src/cmd/list.go
+++ b/src/cmd/list.go
@@ -133,7 +133,8 @@ func getContainers() ([]toolboxContainer, error) {
 	args := []string{"--all", "--sort", "names"}
 	containers, err := podman.GetContainers(args...)
 	if err != nil {
-		return nil, fmt.Errorf("failed to get containers: %w", err)
+		logrus.Debugf("Fetching all containers failed: %s", err)
+		return nil, errors.New("failed to get containers")
 	}
 
 	var toolboxContainers []toolboxContainer
@@ -195,7 +196,8 @@ func getImages() ([]toolboxImage, error) {
 	args := []string{"--sort", "repository"}
 	images, err := podman.GetImages(args...)
 	if err != nil {
-		return nil, fmt.Errorf("failed to get images: %w", err)
+		logrus.Debugf("Fetching all images failed: %s", err)
+		return nil, errors.New("failed to get images")
 	}
 
 	var toolboxImages []toolboxImage
diff --git a/src/cmd/root.go b/src/cmd/root.go
index fc11e5d..ab58d82 100644
--- a/src/cmd/root.go
+++ b/src/cmd/root.go
@@ -203,7 +203,8 @@ func migrate() error {
 
 	configDir, err := os.UserConfigDir()
 	if err != nil {
-		return fmt.Errorf("failed to get the user config directory: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to get the user config directory: %s", err)
+		return errors.New("failed to get the user config directory")
 	}
 
 	toolboxConfigDir := configDir + "/toolbox"
@@ -212,14 +213,19 @@ func migrate() error {
 
 	podmanVersion, err := podman.GetVersion()
 	if err != nil {
-		return fmt.Errorf("failed to get the Podman version: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to get the Podman version: %s", err)
+		return errors.New("failed to get the Podman version")
 	}
 
 	logrus.Debugf("Current Podman version is %s", podmanVersion)
 
 	err = os.MkdirAll(toolboxConfigDir, 0775)
 	if err != nil {
-		return fmt.Errorf("failed to create configuration directory: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to create configuration directory %s: %s",
+			toolboxConfigDir,
+			err)
+
+		return errors.New("failed to create configuration directory")
 	}
 
 	toolboxRuntimeDirectory, err := utils.GetRuntimeDirectory(currentUser)
@@ -231,7 +237,8 @@ func migrate() error {
 
 	migrateLockFile, err := os.Create(migrateLock)
 	if err != nil {
-		return fmt.Errorf("failed to create migration lock file: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to create migration lock file %s: %s", migrateLock, err)
+		return errors.New("failed to create migration lock file")
 	}
 
 	defer migrateLockFile.Close()
@@ -239,13 +246,15 @@ func migrate() error {
 	migrateLockFD := migrateLockFile.Fd()
 	migrateLockFDInt := int(migrateLockFD)
 	if err := syscall.Flock(migrateLockFDInt, syscall.LOCK_EX); err != nil {
-		return fmt.Errorf("failed to acquire migration lock: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to acquire migration lock on %s: %s", migrateLock, err)
+		return errors.New("failed to acquire migration lock")
 	}
 
 	stampBytes, err := ioutil.ReadFile(stampPath)
 	if err != nil {
 		if !os.IsNotExist(err) {
-			return fmt.Errorf("failed to read migration stamp file: %w", err)
+			logrus.Debugf("Migrating to newer Podman: failed to read migration stamp file %s: %s", stampPath, err)
+			return errors.New("failed to read migration stamp file")
 		}
 	} else {
 		stampString := string(stampBytes)
@@ -268,7 +277,8 @@ func migrate() error {
 	}
 
 	if err = podman.SystemMigrate(""); err != nil {
-		return fmt.Errorf("failed to migrate containers: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to migrate containers: %s", err)
+		return errors.New("failed to migrate containers")
 	}
 
 	logrus.Debugf("Migration to Podman version %s was ok", podmanVersion)
@@ -277,7 +287,11 @@ func migrate() error {
 	podmanVersionBytes := []byte(podmanVersion + "\n")
 	err = ioutil.WriteFile(stampPath, podmanVersionBytes, 0664)
 	if err != nil {
-		return fmt.Errorf("failed to update Podman version in migration stamp file: %w", err)
+		logrus.Debugf("Migrating to newer Podman: failed to update Podman version in migration stamp file %s: %s",
+			stampPath,
+			err)
+
+		return errors.New("failed to update Podman version in migration stamp file")
 	}
 
 	return nil
@@ -359,7 +373,8 @@ func setUpLoggers() error {
 func validateSubIDFile(path string) (bool, error) {
 	file, err := os.Open(path)
 	if err != nil {
-		return false, fmt.Errorf("failed to open %s: %w", path, err)
+		logrus.Debugf("Validating sub-ID file: failed to open %s: %s", path, err)
+		return false, fmt.Errorf("failed to open %s", path)
 	}
 
 	scanner := bufio.NewScanner(file)