diff --git a/internal/ai/compat/client.go b/internal/ai/compat/client.go
index ccce7be..42de883 100644
--- a/internal/ai/compat/client.go
+++ b/internal/ai/compat/client.go
@@ -10,6 +10,8 @@ import (
 	"log/slog"
 	"net"
 	"net/http"
+	"regexp"
+	"slices"
 	"strings"
 	"time"
 
@@ -78,6 +80,7 @@ type chatCompletionsRequest struct {
 	Model          string        `json:"model"`
 	Temperature    float64       `json:"temperature,omitempty"`
 	ResponseFormat *responseType `json:"response_format,omitempty"`
+	Stream         *bool         `json:"stream,omitempty"`
 	Messages       []chatMessage `json:"messages"`
 }
 
@@ -109,6 +112,8 @@ type providerError struct {
 	Type    string `json:"type,omitempty"`
 }
 
+const maxMetadataAttempts = 3
+
 func New(cfg Config) *Client {
 	return &Client{
 		name:                  cfg.Name,
@@ -160,7 +165,11 @@ func (c *Client) ExtractMetadata(ctx context.Context, input string) (thoughttype
 	}
 
 	result, err := c.extractMetadataWithModel(ctx, input, c.metadataModel)
-	if err != nil && c.fallbackMetadataModel != "" && ctx.Err() == nil {
+	if err == nil {
+		return result, nil
+	}
+
+	if c.fallbackMetadataModel != "" && ctx.Err() == nil {
 		if c.log != nil {
 			c.log.Warn("metadata extraction failed, trying fallback model",
 				slog.String("provider", c.name),
@@ -169,68 +178,107 @@ func (c *Client) ExtractMetadata(ctx context.Context, input string) (thoughttype
 				slog.String("error", err.Error()),
 			)
 		}
-		return c.extractMetadataWithModel(ctx, input, c.fallbackMetadataModel)
+		fallbackResult, fallbackErr := c.extractMetadataWithModel(ctx, input, c.fallbackMetadataModel)
+		if fallbackErr == nil {
+			return fallbackResult, nil
+		}
+		err = fallbackErr
 	}
-	return result, err
+
+	heuristic := heuristicMetadataFromInput(input)
+	if c.log != nil {
+		c.log.Warn("metadata extraction failed for all models, using heuristic fallback",
+			slog.String("provider", c.name),
+			slog.String("error", err.Error()),
+		)
+	}
+	return heuristic, nil
 }
 
 func (c *Client) extractMetadataWithModel(ctx context.Context, input, model string) (thoughttypes.ThoughtMetadata, error) {
+	stream := false
 	req := chatCompletionsRequest{
 		Model:       model,
 		Temperature: c.temperature,
 		ResponseFormat: &responseType{
 			Type: "json_object",
 		},
+		Stream: &stream,
 		Messages: []chatMessage{
 			{Role: "system", Content: metadataSystemPrompt},
 			{Role: "user", Content: input},
 		},
 	}
 
-	if c.logConversations && c.log != nil {
-		c.log.Info("metadata conversation request",
-			slog.String("provider", c.name),
-			slog.String("model", model),
-			slog.String("system", metadataSystemPrompt),
-			slog.String("input", input),
-		)
+	var lastErr error
+	for attempt := 1; attempt <= maxMetadataAttempts; attempt++ {
+		if c.logConversations && c.log != nil {
+			c.log.Info("metadata conversation request",
+				slog.String("provider", c.name),
+				slog.String("model", model),
+				slog.Int("attempt", attempt),
+				slog.String("system", metadataSystemPrompt),
+				slog.String("input", input),
+			)
+		}
+
+		var resp chatCompletionsResponse
+		if err := c.doJSON(ctx, "/chat/completions", req, &resp); err != nil {
+			return thoughttypes.ThoughtMetadata{}, err
+		}
+		if resp.Error != nil {
+			return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata error: %s", c.name, resp.Error.Message)
+		}
+		if len(resp.Choices) == 0 {
+			return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata: no choices returned", c.name)
+		}
+
+		rawResponse := extractChoiceText(resp.Choices[0].Message, resp.Choices[0].Text)
+
+		if c.logConversations && c.log != nil {
+			c.log.Info("metadata conversation response",
+				slog.String("provider", c.name),
+				slog.String("model", model),
+				slog.Int("attempt", attempt),
+				slog.String("response", rawResponse),
+			)
+		}
+
+		metadataText := strings.TrimSpace(rawResponse)
+		metadataText = stripThinkingBlocks(metadataText)
+		metadataText = stripCodeFence(metadataText)
+		metadataText = extractJSONObject(metadataText)
+		if metadataText == "" {
+			lastErr = fmt.Errorf("%s metadata: response contains no JSON object", c.name)
+			if strings.TrimSpace(rawResponse) == "" && attempt < maxMetadataAttempts && ctx.Err() == nil {
+				if c.log != nil {
+					c.log.Warn("metadata response empty, waiting and retrying",
+						slog.String("provider", c.name),
+						slog.String("model", model),
+						slog.Int("attempt", attempt+1),
+					)
+				}
+				if err := sleepMetadataRetry(ctx, attempt); err != nil {
+					return thoughttypes.ThoughtMetadata{}, err
+				}
+				continue
+			}
+			return thoughttypes.ThoughtMetadata{}, lastErr
+		}
+
+		var metadata thoughttypes.ThoughtMetadata
+		if err := json.Unmarshal([]byte(metadataText), &metadata); err != nil {
+			lastErr = fmt.Errorf("%s metadata: parse json: %w", c.name, err)
+			return thoughttypes.ThoughtMetadata{}, lastErr
+		}
+
+		return metadata, nil
 	}
 
-	var resp chatCompletionsResponse
-	if err := c.doJSON(ctx, "/chat/completions", req, &resp); err != nil {
-		return thoughttypes.ThoughtMetadata{}, err
+	if lastErr != nil {
+		return thoughttypes.ThoughtMetadata{}, lastErr
 	}
-	if resp.Error != nil {
-		return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata error: %s", c.name, resp.Error.Message)
-	}
-	if len(resp.Choices) == 0 {
-		return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata: no choices returned", c.name)
-	}
-
-	rawResponse := extractChoiceText(resp.Choices[0].Message, resp.Choices[0].Text)
-
-	if c.logConversations && c.log != nil {
-		c.log.Info("metadata conversation response",
-			slog.String("provider", c.name),
-			slog.String("model", model),
-			slog.String("response", rawResponse),
-		)
-	}
-
-	metadataText := strings.TrimSpace(rawResponse)
-	metadataText = stripThinkingBlocks(metadataText)
-	metadataText = stripCodeFence(metadataText)
-	metadataText = extractJSONObject(metadataText)
-	if metadataText == "" {
-		return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata: response contains no JSON object", c.name)
-	}
-
-	var metadata thoughttypes.ThoughtMetadata
-	if err := json.Unmarshal([]byte(metadataText), &metadata); err != nil {
-		return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata: parse json: %w", c.name, err)
-	}
-
-	return metadata, nil
+	return thoughttypes.ThoughtMetadata{}, fmt.Errorf("%s metadata: response contains no JSON object", c.name)
 }
 
 func (c *Client) Summarize(ctx context.Context, systemPrompt, userPrompt string) (string, error) {
@@ -484,6 +532,168 @@ func extractTextFromAny(value any) string {
 	return ""
 }
 
+var (
+	monthDatePattern = regexp.MustCompile(`(?i)\b\d{1,2}\s+(?:jan(?:uary)?|feb(?:ruary)?|mar(?:ch)?|apr(?:il)?|may|jun(?:e)?|jul(?:y)?|aug(?:ust)?|sep(?:t(?:ember)?)?|oct(?:ober)?|nov(?:ember)?|dec(?:ember)?)\s+\d{4}\b`)
+	isoDatePattern   = regexp.MustCompile(`\b\d{4}-\d{2}-\d{2}\b`)
+	wordPattern      = regexp.MustCompile(`[a-zA-Z][a-zA-Z0-9_/-]{2,}`)
+)
+
+func heuristicMetadataFromInput(input string) thoughttypes.ThoughtMetadata {
+	text := strings.TrimSpace(input)
+	lower := strings.ToLower(text)
+
+	metadata := thoughttypes.ThoughtMetadata{
+		People:         heuristicPeople(text),
+		ActionItems:    heuristicActionItems(text),
+		DatesMentioned: heuristicDates(text),
+		Topics:         heuristicTopics(lower),
+		Type:           heuristicType(lower),
+		Source:         "",
+	}
+
+	if len(metadata.Topics) == 0 {
+		metadata.Topics = []string{"uncategorized"}
+	}
+	if metadata.Type == "" {
+		metadata.Type = "observation"
+	}
+	return metadata
+}
+
+func heuristicType(lower string) string {
+	switch {
+	case strings.Contains(lower, "preferred name"), strings.Contains(lower, "personal profile"), strings.Contains(lower, "wife:"), strings.Contains(lower, "daughter:"), strings.Contains(lower, "born:"):
+		return "person_note"
+	case strings.Contains(lower, "todo"), strings.Contains(lower, "action item"), strings.Contains(lower, "need to"), strings.Contains(lower, "must "), strings.Contains(lower, "should "):
+		return "task"
+	case strings.Contains(lower, "idea"), strings.Contains(lower, "proposal"), strings.Contains(lower, "brainstorm"):
+		return "idea"
+	case strings.Contains(lower, "reference"), strings.Contains(lower, "rfc "), strings.Contains(lower, "docs"), strings.Contains(lower, "spec"):
+		return "reference"
+	default:
+		return "observation"
+	}
+}
+
+func heuristicTopics(lower string) []string {
+	candidates := []string{
+		"mcp", "auth", "oauth", "api_keys", "token", "middleware", "postgres", "search", "embeddings", "metadata",
+		"go", "server", "project", "memory", "claude", "automation", "calendar", "email", "atlassian", "n8n",
+	}
+
+	topics := make([]string, 0, 6)
+	for _, topic := range candidates {
+		if strings.Contains(lower, topic) {
+			topics = append(topics, topic)
+		}
+		if len(topics) >= 6 {
+			break
+		}
+	}
+
+	if len(topics) > 0 {
+		return topics
+	}
+
+	words := wordPattern.FindAllString(lower, -1)
+	for _, w := range words {
+		if len(w) < 4 {
+			continue
+		}
+		if slices.Contains(topics, w) {
+			continue
+		}
+		topics = append(topics, w)
+		if len(topics) >= 4 {
+			break
+		}
+	}
+	return topics
+}
+
+func heuristicDates(text string) []string {
+	values := make([]string, 0, 4)
+	seen := map[string]struct{}{}
+
+	for _, match := range monthDatePattern.FindAllString(text, -1) {
+		key := strings.ToLower(match)
+		if _, ok := seen[key]; ok {
+			continue
+		}
+		seen[key] = struct{}{}
+		values = append(values, match)
+	}
+
+	for _, match := range isoDatePattern.FindAllString(text, -1) {
+		key := strings.ToLower(match)
+		if _, ok := seen[key]; ok {
+			continue
+		}
+		seen[key] = struct{}{}
+		values = append(values, match)
+	}
+
+	return values
+}
+
+func heuristicPeople(text string) []string {
+	lines := strings.Split(text, "\n")
+	people := make([]string, 0, 4)
+	seen := map[string]struct{}{}
+
+	add := func(name string) {
+		name = strings.TrimSpace(name)
+		if name == "" {
+			return
+		}
+		key := strings.ToLower(name)
+		if _, ok := seen[key]; ok {
+			return
+		}
+		seen[key] = struct{}{}
+		people = append(people, name)
+	}
+
+	for _, line := range lines {
+		l := strings.TrimSpace(line)
+		l = strings.TrimSpace(strings.TrimPrefix(strings.TrimPrefix(l, "-"), "*"))
+		if strings.Contains(strings.ToLower(l), "preferred name") && strings.Contains(l, " is ") {
+			parts := strings.SplitN(l, " is ", 2)
+			add(parts[0])
+		}
+		for _, marker := range []string{"Wife:", "Daughter:", "Son:", "Partner:", "Name:"} {
+			if strings.HasPrefix(l, marker) {
+				rest := strings.TrimSpace(strings.TrimPrefix(l, marker))
+				if idx := strings.Index(rest, ","); idx > 0 {
+					rest = rest[:idx]
+				}
+				add(rest)
+			}
+		}
+	}
+
+	return people
+}
+
+func heuristicActionItems(text string) []string {
+	lines := strings.Split(text, "\n")
+	items := make([]string, 0, 5)
+	for _, line := range lines {
+		l := strings.TrimSpace(strings.TrimPrefix(strings.TrimPrefix(line, "-"), "*"))
+		if l == "" {
+			continue
+		}
+		ll := strings.ToLower(l)
+		if strings.Contains(ll, "todo") || strings.HasPrefix(ll, "fix ") || strings.HasPrefix(ll, "add ") || strings.HasPrefix(ll, "update ") || strings.HasPrefix(ll, "implement ") {
+			items = append(items, l)
+		}
+		if len(items) >= 5 {
+			break
+		}
+	}
+	return items
+}
+
 func isRetryableStatus(status int) bool {
 	switch status {
 	case http.StatusTooManyRequests, http.StatusInternalServerError, http.StatusBadGateway, http.StatusServiceUnavailable, http.StatusGatewayTimeout:
@@ -518,3 +728,15 @@ func sleepRetry(ctx context.Context, attempt int, log *slog.Logger, provider str
 		return nil
 	}
 }
+
+func sleepMetadataRetry(ctx context.Context, attempt int) error {
+	delay := time.Duration(attempt) * 350 * time.Millisecond
+	timer := time.NewTimer(delay)
+	defer timer.Stop()
+	select {
+	case <-ctx.Done():
+		return ctx.Err()
+	case <-timer.C:
+		return nil
+	}
+}
diff --git a/internal/ai/compat/client_test.go b/internal/ai/compat/client_test.go
index df0cd28..a79d518 100644
--- a/internal/ai/compat/client_test.go
+++ b/internal/ai/compat/client_test.go
@@ -7,6 +7,7 @@ import (
 	"log/slog"
 	"net/http"
 	"net/http/httptest"
+	"strings"
 	"sync/atomic"
 	"testing"
 )
@@ -250,3 +251,93 @@ func TestExtractMetadataUsesReasoningContentWhenContentEmpty(t *testing.T) {
 		t.Fatalf("metadata people = %#v, want [Hein]", metadata.People)
 	}
 }
+
+func TestExtractMetadataFallsBackToHeuristicsWhenModelsFail(t *testing.T) {
+	var calls atomic.Int32
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		_ = calls.Add(1)
+		_ = json.NewEncoder(w).Encode(map[string]any{
+			"choices": []map[string]any{
+				{"message": map[string]any{"content": "not json"}},
+			},
+		})
+	}))
+	defer server.Close()
+
+	client := New(Config{
+		Name:                  "test",
+		BaseURL:               server.URL,
+		APIKey:                "secret",
+		MetadataModel:         "primary",
+		FallbackMetadataModel: "secondary",
+		HTTPClient:            server.Client(),
+		Log:                   discardLogger(),
+	})
+
+	input := "Personal profile - Hein (Warkanum):\n- Born: 23 May 1989\n- Wife: Cindy, born 16 November 1994"
+	metadata, err := client.ExtractMetadata(context.Background(), input)
+	if err != nil {
+		t.Fatalf("ExtractMetadata() error = %v", err)
+	}
+	if calls.Load() != 2 {
+		t.Fatalf("call count = %d, want 2", calls.Load())
+	}
+	if metadata.Type != "person_note" {
+		t.Fatalf("metadata type = %q, want person_note", metadata.Type)
+	}
+	if len(metadata.DatesMentioned) < 2 {
+		t.Fatalf("metadata dates = %#v, want extracted dates", metadata.DatesMentioned)
+	}
+	if len(metadata.People) == 0 || !strings.EqualFold(metadata.People[0], "Cindy") {
+		t.Fatalf("metadata people = %#v, want Cindy", metadata.People)
+	}
+}
+
+func TestExtractMetadataRetriesEmptyResponse(t *testing.T) {
+	var calls atomic.Int32
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		call := calls.Add(1)
+		var req chatCompletionsRequest
+		_ = json.NewDecoder(r.Body).Decode(&req)
+
+		if req.Stream == nil || *req.Stream {
+			t.Fatalf("expected stream=false, got %#v", req.Stream)
+		}
+
+		if call == 1 {
+			_ = json.NewEncoder(w).Encode(map[string]any{
+				"choices": []map[string]any{
+					{"message": map[string]any{"content": ""}},
+				},
+			})
+			return
+		}
+
+		_ = json.NewEncoder(w).Encode(map[string]any{
+			"choices": []map[string]any{
+				{"message": map[string]any{"content": "{\"people\":[],\"action_items\":[],\"dates_mentioned\":[],\"topics\":[\"mcp\"],\"type\":\"observation\",\"source\":\"mcp\"}"}},
+			},
+		})
+	}))
+	defer server.Close()
+
+	client := New(Config{
+		Name:          "test",
+		BaseURL:       server.URL,
+		APIKey:        "secret",
+		MetadataModel: "meta-model",
+		HTTPClient:    server.Client(),
+		Log:           discardLogger(),
+	})
+
+	metadata, err := client.ExtractMetadata(context.Background(), "hello")
+	if err != nil {
+		t.Fatalf("ExtractMetadata() error = %v", err)
+	}
+	if calls.Load() < 2 {
+		t.Fatalf("call count = %d, want >= 2", calls.Load())
+	}
+	if metadata.Type != "observation" {
+		t.Fatalf("metadata type = %q, want observation", metadata.Type)
+	}
+}