diff --git a/server/routes.go b/server/routes.go
index cc891353..ae166214 100644
--- a/server/routes.go
+++ b/server/routes.go
@@ -1673,6 +1673,10 @@ func (s *Server) ChatHandler(c *gin.Context) {
 			OpeningTag: openingTag,
 			ClosingTag: closingTag,
 		}
+
+		if strings.HasSuffix(strings.TrimSpace(prompt), openingTag) {
+			thinkingState.AddContent(openingTag)
+		}
 	}
 
 	var toolParser *tools.Parser
diff --git a/server/routes_generate_test.go b/server/routes_generate_test.go
index a57975f1..a3b83fc1 100644
--- a/server/routes_generate_test.go
+++ b/server/routes_generate_test.go
@@ -969,3 +969,233 @@ func TestGenerate(t *testing.T) {
 		}
 	})
 }
+
+func TestChatWithPromptEndingInThinkTag(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+
+	// Helper to create a standard thinking test setup
+	setupThinkingTest := func(t *testing.T) (*mockRunner, *Server) {
+		mock := &mockRunner{
+			CompletionResponse: llm.CompletionResponse{
+				Done:               true,
+				DoneReason:         llm.DoneReasonStop,
+				PromptEvalCount:    1,
+				PromptEvalDuration: 1,
+				EvalCount:          1,
+				EvalDuration:       1,
+			},
+		}
+
+		s := &Server{
+			sched: &Scheduler{
+				pendingReqCh:  make(chan *LlmRequest, 1),
+				finishedReqCh: make(chan *LlmRequest, 1),
+				expiredCh:     make(chan *runnerRef, 1),
+				unloadedCh:    make(chan any, 1),
+				loaded:        make(map[string]*runnerRef),
+				newServerFn:   newMockServer(mock),
+				getGpuFn:      discover.GetGPUInfo,
+				getCpuFn:      discover.GetCPUInfo,
+				reschedDelay:  250 * time.Millisecond,
+				loadFn: func(req *LlmRequest, _ *ggml.GGML, _ discover.GpuInfoList, _ bool) bool {
+					time.Sleep(time.Millisecond)
+					req.successCh <- &runnerRef{llama: mock}
+					return false
+				},
+			},
+		}
+
+		go s.sched.Run(t.Context())
+
+		// Create a model with thinking support
+		_, digest := createBinFile(t, ggml.KV{
+			"general.architecture":          "llama",
+			"llama.block_count":             uint32(1),
+			"llama.context_length":          uint32(8192),
+			"llama.embedding_length":        uint32(4096),
+			"llama.attention.head_count":    uint32(32),
+			"llama.attention.head_count_kv": uint32(8),
+			"tokenizer.ggml.tokens":         []string{""},
+			"tokenizer.ggml.scores":         []float32{0},
+			"tokenizer.ggml.token_type":     []int32{0},
+		}, []*ggml.Tensor{
+			{Name: "token_embd.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.attn_norm.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.ffn_down.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.ffn_gate.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.ffn_up.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.ffn_norm.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.attn_k.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.attn_output.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.attn_q.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "blk.0.attn_v.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+			{Name: "output.weight", Shape: []uint64{1}, WriterTo: bytes.NewReader(make([]byte, 4))},
+		})
+
+		// Create model with thinking template that adds <think> at the end
+		w := createRequest(t, s.CreateHandler, api.CreateRequest{
+			Model: "test-thinking",
+			Files: map[string]string{"file.gguf": digest},
+			Template: `{{- range .Messages }}
+{{- if eq .Role "user" }}user: {{ .Content }}
+{{ else if eq .Role "assistant" }}assistant: {{ if .Thinking }}<think>{{ .Thinking }}</think>{{ end }}{{ .Content }}
+{{ end }}{{ end }}<think>`,
+			Stream: &stream,
+		})
+
+		if w.Code != http.StatusOK {
+			t.Fatalf("expected status 200, got %d", w.Code)
+		}
+
+		return mock, s
+	}
+
+	mock, s := setupThinkingTest(t)
+
+	// Helper to test chat responses
+	testChatRequest := func(t *testing.T, name string, userContent string, modelResponse string, expectedThinking string, expectedContent string, think bool) {
+		t.Run(name, func(t *testing.T) {
+			mock.CompletionResponse = llm.CompletionResponse{
+				Content:            modelResponse,
+				Done:               true,
+				DoneReason:         llm.DoneReasonStop,
+				PromptEvalCount:    1,
+				PromptEvalDuration: 1,
+				EvalCount:          1,
+				EvalDuration:       1,
+			}
+			mock.CompletionFn = nil
+
+			streamRequest := false
+			req := api.ChatRequest{
+				Model: "test-thinking",
+				Messages: []api.Message{
+					{Role: "user", Content: userContent},
+				},
+				Stream: &streamRequest,
+			}
+			if think {
+				req.Think = &api.ThinkValue{Value: think}
+			}
+
+			w := createRequest(t, s.ChatHandler, req)
+			if w.Code != http.StatusOK {
+				t.Fatalf("expected status 200, got %d", w.Code)
+			}
+
+			var resp api.ChatResponse
+			if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+				t.Fatal(err)
+			}
+
+			if resp.Message.Thinking != expectedThinking {
+				t.Errorf("expected thinking %q, got %q", expectedThinking, resp.Message.Thinking)
+			}
+
+			if resp.Message.Content != expectedContent {
+				t.Errorf("expected content %q, got %q", expectedContent, resp.Message.Content)
+			}
+		})
+	}
+
+	// Test cases - Note: Template adds <think> at the end, and leading whitespace after <think> is eaten by the parser
+	testChatRequest(t, "basic thinking response",
+		"Help me solve this problem",
+		" Let me think about this step by step... </think> The answer is 42.",
+		"Let me think about this step by step... ",
+		"The answer is 42.",
+		true)
+
+	testChatRequest(t, "thinking with multiple sentences",
+		"Explain quantum computing",
+		" First, I need to understand the basics. Quantum bits can be in superposition. </think> Quantum computing uses quantum mechanics principles.",
+		"First, I need to understand the basics. Quantum bits can be in superposition. ",
+		"Quantum computing uses quantum mechanics principles.",
+		true)
+
+	testChatRequest(t, "no thinking content",
+		"What is 2+2?",
+		"</think> The answer is 4.",
+		"",
+		"The answer is 4.",
+		true)
+
+	testChatRequest(t, "thinking disabled but template still adds think tag",
+		"Simple question",
+		" My thoughts </think> The answer.",
+		"",
+		" My thoughts </think> The answer.",
+		false)
+
+	// Test streaming response with template-added <think>
+	t.Run("streaming with thinking", func(t *testing.T) {
+		var wg sync.WaitGroup
+		wg.Add(1)
+
+		mock.CompletionFn = func(ctx context.Context, r llm.CompletionRequest, fn func(r llm.CompletionResponse)) error {
+			defer wg.Done()
+
+			// Verify the prompt ends with <think> due to template
+			if !strings.HasSuffix(r.Prompt, "<think>") {
+				t.Errorf("expected prompt to end with <think>, got: %q", r.Prompt)
+			}
+
+			// Simulate streaming chunks
+			responses := []llm.CompletionResponse{
+				{Content: " I need to consider", Done: false, PromptEvalCount: 1, PromptEvalDuration: 1},
+				{Content: " multiple factors here...", Done: false, PromptEvalCount: 1, PromptEvalDuration: 1},
+				{Content: " </think> Based on my analysis,", Done: false, PromptEvalCount: 1, PromptEvalDuration: 1},
+				{Content: " the solution is straightforward.", Done: true, DoneReason: llm.DoneReasonStop, PromptEvalCount: 1, PromptEvalDuration: 1, EvalCount: 1, EvalDuration: 1},
+			}
+
+			for _, resp := range responses {
+				select {
+				case <-ctx.Done():
+					return ctx.Err()
+				default:
+					fn(resp)
+					time.Sleep(10 * time.Millisecond)
+				}
+			}
+			return nil
+		}
+
+		think := true
+		w := createRequest(t, s.ChatHandler, api.ChatRequest{
+			Model:    "test-thinking",
+			Messages: []api.Message{{Role: "user", Content: "Analyze this complex problem"}},
+			Think:    &api.ThinkValue{Value: think},
+			Stream:   &stream,
+		})
+
+		wg.Wait()
+
+		if w.Code != http.StatusOK {
+			t.Fatalf("expected status 200, got %d", w.Code)
+		}
+
+		// Parse streaming responses
+		decoder := json.NewDecoder(w.Body)
+		var allThinking, allContent strings.Builder
+
+		for {
+			var resp api.ChatResponse
+			if err := decoder.Decode(&resp); err == io.EOF {
+				break
+			} else if err != nil {
+				t.Fatal(err)
+			}
+			allThinking.WriteString(resp.Message.Thinking)
+			allContent.WriteString(resp.Message.Content)
+		}
+
+		// Note: Leading whitespace after <think> is eaten by the parser
+		if got := allThinking.String(); got != "I need to consider multiple factors here... " {
+			t.Errorf("expected thinking %q, got %q", "I need to consider multiple factors here... ", got)
+		}
+
+		if got := allContent.String(); got != "Based on my analysis, the solution is straightforward." {
+			t.Errorf("expected content %q, got %q", "Based on my analysis, the solution is straightforward.", got)
+		}
+	})
+}