diff --git a/pkg/docker/login.go b/pkg/docker/login.go
index 2110224a06..2e52528076 100644
--- a/pkg/docker/login.go
+++ b/pkg/docker/login.go
@@ -45,7 +45,8 @@ func saveAuthToCredentialsStore(ctx context.Context, credsStore string, registry
 	}
 	cmd := exec.CommandContext(ctx, binary, "store") //nolint:gosec // G702: binary is from Docker config, not user input
 	cmd.Env = os.Environ()
-	cmd.Stderr = os.Stderr
+	var stderr strings.Builder
+	cmd.Stderr = &stderr
 	stdin, err := cmd.StdinPipe()
 	if err != nil {
 		return fmt.Errorf("Failed to connect stdin to %s: %w", binary, err)
@@ -61,6 +62,13 @@ func saveAuthToCredentialsStore(ctx context.Context, credsStore string, registry
 		return fmt.Errorf("Failed to close stdin to %s: %w", binary, err)
 	}
 	if err := cmd.Wait(); err != nil {
+		output := strings.TrimSpace(stderr.String())
+		if strings.Contains(strings.ToLower(output), "pass not initialized") {
+			return fmt.Errorf("failed to store Docker credentials because `pass` is not initialized; create a GPG key with `gpg --generate-key`, initialize the password store with `pass init <gpg-id>`, then run `cog login` again")
+		}
+		if output != "" {
+			return fmt.Errorf("Failed to run %s: %s", binary, output)
+		}
 		return fmt.Errorf("Failed to run %s: %w", binary, err)
 	}
 	return nil
diff --git a/pkg/docker/login_test.go b/pkg/docker/login_test.go
new file mode 100644
index 0000000000..fbd527a837
--- /dev/null
+++ b/pkg/docker/login_test.go
@@ -0,0 +1,34 @@
+package docker
+
+import (
+	"os"
+	"path/filepath"
+	"runtime"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestSaveAuthToCredentialsStorePassNotInitialized(t *testing.T) {
+	if runtime.GOOS == "windows" {
+		t.Skip("test credential helper is a shell script")
+	}
+
+	binDir := t.TempDir()
+	helperPath := filepath.Join(binDir, "docker-credential-test")
+	helper := `#!/bin/sh
+cat >/dev/null
+echo "pass not initialized: exit status 1" >&2
+exit 1
+`
+	require.NoError(t, os.WriteFile(helperPath, []byte(helper), 0o755))
+	t.Setenv("PATH", binDir+string(os.PathListSeparator)+os.Getenv("PATH"))
+
+	err := saveAuthToCredentialsStore(t.Context(), "test", "r8.im", "test-user", "secret-token")
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "`pass` is not initialized")
+	assert.Contains(t, err.Error(), "gpg --generate-key")
+	assert.Contains(t, err.Error(), "pass init <gpg-id>")
+	assert.NotContains(t, err.Error(), "secret-token")
+}