diff --git a/plugins/ai/anthropic/anthropic.go b/plugins/ai/anthropic/anthropic.go
index a755c8c7..7f0dfe24 100644
--- a/plugins/ai/anthropic/anthropic.go
+++ b/plugins/ai/anthropic/anthropic.go
@@ -117,8 +117,14 @@ func (t *oauthTransport) getValidToken() (string, error) {
 	if err != nil {
 		return "", fmt.Errorf("failed to load stored token: %w", err)
 	}
+	// If no token exists, run OAuth flow
 	if token == nil {
-		return "", fmt.Errorf("no OAuth token stored, please re-authenticate")
+		fmt.Println("No OAuth token found, initiating authentication...")
+		newAccessToken, err := runOAuthFlow()
+		if err != nil {
+			return "", fmt.Errorf("failed to authenticate: %w", err)
+		}
+		return newAccessToken, nil
 	}
 
 	// Check if token needs refresh (5 minute buffer)
@@ -126,7 +132,12 @@ func (t *oauthTransport) getValidToken() (string, error) {
 		fmt.Println("OAuth token expired, refreshing...")
 		newAccessToken, err := refreshToken()
 		if err != nil {
-			return "", fmt.Errorf("failed to refresh token: %w", err)
+			// If refresh fails, try re-authentication
+			fmt.Println("Token refresh failed, re-authenticating...")
+			newAccessToken, err = runOAuthFlow()
+			if err != nil {
+				return "", fmt.Errorf("failed to refresh or re-authenticate: %w", err)
+			}
 		}
 
 		return newAccessToken, nil
@@ -584,3 +595,182 @@ func refreshToken() (string, error) {
 
 	return result.AccessToken, nil
 }
+
+// runOAuthFlowWithTimeout runs the OAuth flow with an extended timeout for user interaction
+func runOAuthFlowWithTimeout() (string, error) {
+	// Use a longer timeout context for OAuth flows (10 minutes)
+	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Minute)
+	defer cancel()
+
+	// Store the context for use in HTTP requests
+	return runOAuthFlowWithContext(ctx)
+}
+
+// refreshTokenWithTimeout refreshes a token with extended timeout
+func refreshTokenWithTimeout() (string, error) {
+	// Use a longer timeout context for token refresh (2 minutes)
+	ctx, cancel := context.WithTimeout(context.Background(), 2*time.Minute)
+	defer cancel()
+
+	return refreshTokenWithContext(ctx)
+}
+
+// runOAuthFlowWithContext runs OAuth flow with the provided context
+func runOAuthFlowWithContext(ctx context.Context) (string, error) {
+	verifier, challenge, err := generatePKCE()
+	if err != nil {
+		return "", err
+	}
+
+	cfg := oauth2.Config{
+		ClientID:    oauthClientID,
+		Endpoint:    oauth2.Endpoint{AuthURL: oauthAuthURL, TokenURL: oauthTokenURL},
+		RedirectURL: oauthRedirectURL,
+		Scopes:      []string{"org:create_api_key", "user:profile", "user:inference"},
+	}
+
+	authURL := cfg.AuthCodeURL(verifier,
+		oauth2.SetAuthURLParam("code_challenge", challenge),
+		oauth2.SetAuthURLParam("code_challenge_method", "S256"),
+		oauth2.SetAuthURLParam("code", "true"),
+		oauth2.SetAuthURLParam("state", verifier),
+	)
+
+	fmt.Println("Open the following URL in your browser. Fabric would like to authorize:")
+	fmt.Println(authURL)
+	openBrowser(authURL)
+	fmt.Print("Paste the authorization code here: ")
+
+	// Create a channel to receive the user input
+	codeChan := make(chan string, 1)
+	errChan := make(chan error, 1)
+
+	go func() {
+		var code string
+		_, err := fmt.Scanln(&code)
+		if err != nil {
+			errChan <- err
+			return
+		}
+		codeChan <- code
+	}()
+
+	// Wait for either user input or context timeout
+	var code string
+	select {
+	case code = <-codeChan:
+		// User provided input
+	case err := <-errChan:
+		return "", fmt.Errorf("failed to read authorization code: %w", err)
+	case <-ctx.Done():
+		return "", fmt.Errorf("authentication timed out - please try again")
+	}
+
+	parts := strings.SplitN(code, "#", 2)
+	state := verifier
+	if len(parts) == 2 {
+		state = parts[1]
+	}
+
+	// Manual token exchange to match opencode implementation
+	tokenReq := map[string]string{
+		"code":          parts[0],
+		"state":         state,
+		"grant_type":    "authorization_code",
+		"client_id":     oauthClientID,
+		"redirect_uri":  oauthRedirectURL,
+		"code_verifier": verifier,
+	}
+
+	return exchangeTokenWithContext(ctx, tokenReq)
+}
+
+// refreshTokenWithContext refreshes a token with the provided context
+func refreshTokenWithContext(ctx context.Context) (string, error) {
+	storage, err := common.NewOAuthStorage()
+	if err != nil {
+		return "", fmt.Errorf("failed to create OAuth storage: %w", err)
+	}
+
+	// Load existing token
+	token, err := storage.LoadToken("claude")
+	if err != nil {
+		return "", fmt.Errorf("failed to load stored token: %w", err)
+	}
+	if token == nil || token.RefreshToken == "" {
+		return "", fmt.Errorf("no refresh token available")
+	}
+
+	// Prepare refresh request
+	refreshReq := map[string]string{
+		"grant_type":    "refresh_token",
+		"refresh_token": token.RefreshToken,
+		"client_id":     oauthClientID,
+	}
+
+	return exchangeTokenWithContext(ctx, refreshReq)
+}
+
+// exchangeTokenWithContext exchanges tokens with the provided context
+func exchangeTokenWithContext(ctx context.Context, params map[string]string) (string, error) {
+	reqBody, err := json.Marshal(params)
+	if err != nil {
+		return "", err
+	}
+
+	req, err := http.NewRequestWithContext(ctx, "POST", oauthTokenURL, bytes.NewBuffer(reqBody))
+	if err != nil {
+		return "", fmt.Errorf("failed to create request: %w", err)
+	}
+	req.Header.Set("Content-Type", "application/json")
+
+	client := &http.Client{}
+	resp, err := client.Do(req)
+	if err != nil {
+		return "", fmt.Errorf("token exchange request failed: %w", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		body, _ := io.ReadAll(resp.Body)
+		return "", fmt.Errorf("token exchange failed: %s - %s", resp.Status, string(body))
+	}
+
+	var result struct {
+		AccessToken  string `json:"access_token"`
+		RefreshToken string `json:"refresh_token"`
+		ExpiresIn    int    `json:"expires_in"`
+		TokenType    string `json:"token_type"`
+		Scope        string `json:"scope"`
+	}
+	if err = json.NewDecoder(resp.Body).Decode(&result); err != nil {
+		return "", fmt.Errorf("failed to parse token response: %w", err)
+	}
+
+	// Save the complete token information
+	storage, err := common.NewOAuthStorage()
+	if err != nil {
+		return "", fmt.Errorf("failed to create OAuth storage: %w", err)
+	}
+
+	oauthToken := &common.OAuthToken{
+		AccessToken:  result.AccessToken,
+		RefreshToken: result.RefreshToken,
+		ExpiresAt:    time.Now().Unix() + int64(result.ExpiresIn),
+		TokenType:    result.TokenType,
+		Scope:        result.Scope,
+	}
+
+	// Use existing refresh token if new one not provided (for refresh operations)
+	if oauthToken.RefreshToken == "" && params["grant_type"] == "refresh_token" {
+		if existingToken, err := storage.LoadToken("claude"); err == nil && existingToken != nil {
+			oauthToken.RefreshToken = existingToken.RefreshToken
+		}
+	}
+
+	if err = storage.SaveToken("claude", oauthToken); err != nil {
+		return "", fmt.Errorf("failed to save OAuth token: %w", err)
+	}
+
+	return result.AccessToken, nil
+}