diff --git a/.github/workflows/pythonTests.yml b/.github/workflows/pythonTests.yml
index ac635e67c..da1f3a616 100644
--- a/.github/workflows/pythonTests.yml
+++ b/.github/workflows/pythonTests.yml
@@ -59,7 +59,7 @@ jobs:
 
       - name: Setup Pipenv
         if: ${{ matrix.suite == 'pipenv' && matrix.os.name != 'macos' }}
-        run: python -m pip install pipenv
+        run: python -m pip install pipenv==2026.2.2
 
       - name: Setup Twine
         if: ${{ matrix.suite == 'pip' && matrix.os.name != 'macos' }}
diff --git a/buildtools/cli.go b/buildtools/cli.go
index 1e8b708a0..4153628c3 100644
--- a/buildtools/cli.go
+++ b/buildtools/cli.go
@@ -1070,7 +1070,7 @@ func buildCmd(c *cli.Context) error {
 	}
 
 	// Extract build configuration and arguments
-	_, rtDetails, _, _, _, cleanArgs, buildConfiguration, err := extractDockerOptionsFromArgs(c.Args())
+	_, rtDetails, _, skipLogin, _, cleanArgs, buildConfiguration, err := extractDockerOptionsFromArgs(c.Args())
 	if err != nil {
 		return err
 	}
@@ -1079,10 +1079,11 @@ func buildCmd(c *cli.Context) error {
 		return err
 	}
 
-	// Login to the docker registry
-	err = loginCmd(c)
-	if err != nil {
-		return err
+	if !skipLogin {
+		err = loginCmd(c)
+		if err != nil {
+			return err
+		}
 	}
 
 	dockerOptions := strategies.DockerBuildOptions{
diff --git a/docker_test.go b/docker_test.go
index 1598b5241..e777dd121 100644
--- a/docker_test.go
+++ b/docker_test.go
@@ -14,6 +14,7 @@ import (
 	"testing"
 	"time"
 
+	urfavecli "github.com/urfave/cli"
 	"github.com/jfrog/jfrog-client-go/utils/log"
 
 	tests2 "github.com/jfrog/jfrog-cli-artifactory/utils/tests"
@@ -1278,6 +1279,48 @@ CMD ["echo", "Hello from buildx"]`, baseImage)
 	inttestutils.ContainerTestCleanup(t, serverDetails, artHttpDetails, imageNameOnly, buildName, tests.OciLocalRepo)
 }
 
+// TestDockerBuildxSkipLoginFails verifies that --skip-login actually skips login.
+// After logging out, buildx --push with --skip-login should fail because no auth is available.
+func TestDockerBuildxSkipLoginFails(t *testing.T) {
+	cleanup := initDockerBuildTest(t)
+	defer cleanup()
+
+	// Prevent urfave/cli from calling os.Exit on command errors
+	origOsExiter := urfavecli.OsExiter
+	urfavecli.OsExiter = func(code int) {}
+	defer func() { urfavecli.OsExiter = origOsExiter }()
+
+	registryHost := *tests.ContainerRegistry
+	if parsedURL, err := url.Parse(registryHost); err == nil && parsedURL.Host != "" {
+		registryHost = parsedURL.Host
+	}
+	imageName := path.Join(registryHost, tests.OciLocalRepo, "test-skip-login")
+	imageTag := imageName + ":v1"
+
+	workspace, err := filepath.Abs(tests.Out)
+	assert.NoError(t, err)
+	assert.NoError(t, fileutils.CreateDirIfNotExist(workspace))
+
+	baseImage := path.Join(registryHost, tests.OciRemoteRepo, "busybox:latest")
+	dockerfileContent := fmt.Sprintf(`FROM %s
+CMD ["echo", "skip-login test"]`, baseImage)
+	dockerfilePath := filepath.Join(workspace, "Dockerfile")
+	assert.NoError(t, os.WriteFile(dockerfilePath, []byte(dockerfileContent), 0644)) //#nosec G703 -- test code
+
+	// Logout from registry so push requires fresh login
+	logoutCmd := exec.Command("docker", "logout", registryHost)
+	assert.NoError(t, logoutCmd.Run())
+
+	// With --skip-login, jf should NOT re-login, so push should fail
+	err = runJfrogCliWithoutAssertion("docker", "buildx", "build",
+		"--platform", "linux/amd64",
+		"-t", imageTag, "-f", dockerfilePath, "--push", "--skip-login", workspace)
+	assert.Error(t, err, "Expected failure: --skip-login should prevent auto-login, causing push to fail without auth")
+
+	// Re-login for subsequent tests
+	runJfrogCli(t, "docker", "login", registryHost)
+}
+
 // TestDockerBuildWithVirtualRepo tests docker build with virtual repository
 func TestDockerBuildWithVirtualRepo(t *testing.T) {
 	cleanup := initDockerBuildTest(t)
diff --git a/utils/cliutils/commandsflags.go b/utils/cliutils/commandsflags.go
index 900b4a242..feafcc4b4 100644
--- a/utils/cliutils/commandsflags.go
+++ b/utils/cliutils/commandsflags.go
@@ -1914,7 +1914,7 @@ var commandFlags = map[string][]string{
 		serverId, skipLogin,
 	},
 	DockerBuild: {
-		BuildName, BuildNumber, serverId,
+		BuildName, BuildNumber, serverId, skipLogin,
 	},
 	DockerPromote: {
 		targetDockerImage, sourceTag, targetTag, dockerPromoteCopy, url, user, password, accessToken, sshPassphrase, sshKeyPath,