diff --git a/internal/login/errors_test.go b/internal/login/errors_test.go
new file mode 100644
index 0000000..851489c
--- /dev/null
+++ b/internal/login/errors_test.go
@@ -0,0 +1,14 @@
+package login
+
+import (
+	"errors"
+	"fmt"
+	"testing"
+)
+
+func TestNoRemoteDebugEndpointIsWrappable(t *testing.T) {
+	wrapped := fmt.Errorf("firstAvailableRemoteDebugEndpoint: %w", errNoRemoteDebugEndpoint)
+	if !errors.Is(wrapped, errNoRemoteDebugEndpoint) {
+		t.Fatalf("errors.Is should report wrapped error as errNoRemoteDebugEndpoint, got false")
+	}
+}
diff --git a/internal/login/login.go b/internal/login/login.go
index 58219bc..b44883a 100644
--- a/internal/login/login.go
+++ b/internal/login/login.go
@@ -496,13 +496,13 @@ func ensureProfileExists(userDataDir, profileDirectory string) error {
 
 func copyBrowserProfileSnapshot(srcUserData, dstUserData, profileDirectory string) error {
 	if err := os.MkdirAll(dstUserData, 0o700); err != nil {
-		return err
+		return fmt.Errorf("create snapshot user data dir: %w", err)
 	}
 	localStateSrc := filepath.Join(srcUserData, "Local State")
 	localStateDst := filepath.Join(dstUserData, "Local State")
 	if _, err := os.Stat(localStateSrc); err == nil {
 		if err := copyFile(localStateSrc, localStateDst); err != nil {
-			return err
+			return fmt.Errorf("copy browser Local State: %w", err)
 		}
 	}
 	srcProfile := filepath.Join(srcUserData, profileDirectory)
@@ -557,23 +557,23 @@ func copyDirFiltered(src, dst string, skip func(rel string, d fs.DirEntry) bool)
 func copyFile(src, dst string) error {
 	in, err := os.Open(src)
 	if err != nil {
-		return err
+		return fmt.Errorf("open source file %s: %w", src, err)
 	}
 	defer func() { _ = in.Close() }()
 	info, err := in.Stat()
 	if err != nil {
-		return err
+		return fmt.Errorf("stat source file %s: %w", src, err)
 	}
 	if err := os.MkdirAll(filepath.Dir(dst), 0o700); err != nil {
-		return err
+		return fmt.Errorf("create destination dir for %s: %w", dst, err)
 	}
 	out, err := os.OpenFile(dst, os.O_CREATE|os.O_WRONLY|os.O_TRUNC, info.Mode())
 	if err != nil {
-		return err
+		return fmt.Errorf("create destination file %s: %w", dst, err)
 	}
 	defer func() { _ = out.Close() }()
 	if _, err := io.Copy(out, in); err != nil {
-		return err
+		return fmt.Errorf("copy file contents to %s: %w", dst, err)
 	}
 	return out.Chmod(info.Mode())
 }
diff --git a/internal/login/remote_debug.go b/internal/login/remote_debug.go
index 4ab43ee..9aef477 100644
--- a/internal/login/remote_debug.go
+++ b/internal/login/remote_debug.go
@@ -216,7 +216,7 @@ func remoteDebugGetJSON(rawURL string, dest any) error {
 	client := &http.Client{Timeout: 2 * time.Second}
 	resp, err := client.Get(rawURL)
 	if err != nil {
-		return err
+		return fmt.Errorf("GET %s: %w", rawURL, err)
 	}
 	defer func() { _ = resp.Body.Close() }()
 	if resp.StatusCode < 200 || resp.StatusCode >= 300 {