diff --git a/bundle/deploy/lock/acquire.go b/bundle/deploy/lock/acquire.go
index 18778aa5dd9..1335f7800c2 100644
--- a/bundle/deploy/lock/acquire.go
+++ b/bundle/deploy/lock/acquire.go
@@ -2,8 +2,11 @@ package lock
 
 import (
 	"context"
+	"errors"
+	"fmt"
 
 	"github.com/databricks/cli/bundle"
+	"github.com/databricks/cli/libs/filer"
 	"github.com/databricks/cli/libs/locker"
 	"github.com/databricks/cli/libs/log"
 )
@@ -47,6 +50,13 @@ func (m *acquire) Apply(ctx context.Context, b *bundle.Bundle) error {
 	err = b.Locker.Lock(ctx, force)
 	if err != nil {
 		log.Errorf(ctx, "Failed to acquire deployment lock: %v", err)
+
+		notExistsError := filer.NoSuchDirectoryError{}
+		if errors.As(err, &notExistsError) {
+			// If we get a "doesn't exist" error from the API this indicates
+			// we either don't have permissions or the path is invalid.
+			return fmt.Errorf("cannot write to deployment root (this can indicate a previous deploy was done with a different identity): %s", b.Config.Workspace.RootPath)
+		}
 		return err
 	}