diff --git a/coderd/x/chatd/chatd_test.go b/coderd/x/chatd/chatd_test.go
index dc3a7ac25e..cad53b9ff7 100644
--- a/coderd/x/chatd/chatd_test.go
+++ b/coderd/x/chatd/chatd_test.go
@@ -5236,22 +5236,25 @@ func highUsageTextResponse(text string) chattest.AnthropicResponse {
 	}, text)...)
 }
 
-func anthropicCompactionResponse(text string) chattest.AnthropicResponse {
-	return chattest.AnthropicResponse{Response: &chattest.AnthropicMessage{
-		ID:         "msg-compaction",
-		Type:       "message",
-		Role:       "assistant",
-		Content:    text,
-		Model:      "claude-3-opus-20240229",
-		StopReason: "end_turn",
-	}}
+func anthropicCompactionResponse(t testing.TB, req *chattest.AnthropicRequest, text string) chattest.AnthropicResponse {
+	t.Helper()
+	require.True(t, req.Stream)
+	// The summary cap is the configured cap with headroom bounded by
+	// the remaining context window, so it varies per test fixture; exact
+	// values are pinned in the chatloop unit tests and the hook test.
+	require.Positive(t, req.MaxTokens)
+	return chattest.AnthropicStreamingResponse(chattest.AnthropicTextChunks(text)...)
 }
 
 func highUsageReadFileResponse(path string) chattest.AnthropicResponse {
+	return readFileResponseWithInputTokens(path, 80)
+}
+
+func readFileResponseWithInputTokens(path string, inputTokens int) chattest.AnthropicResponse {
 	chunks := chattest.AnthropicToolCallChunks("read_file", fmt.Sprintf(`{"path":%q}`, path))
 	for i := range chunks {
 		if chunks[i].Type == "message_start" {
-			chunks[i].Message.Usage = map[string]int{"input_tokens": 80}
+			chunks[i].Message.Usage = map[string]int{"input_tokens": inputTokens}
 		}
 		if chunks[i].Type == "message_delta" {
 			chunks[i].UsageMap = map[string]int{"output_tokens": 5}
@@ -5275,10 +5278,10 @@ func TestActiveServer_RoutingPreservesAPIKeyAfterCompaction(t *testing.T) {
 	var streamCount atomic.Int32
 	anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 		body := anthropicRequestBody(t, *req)
+		if strings.Contains(body, "You are performing a context compaction") {
+			return anthropicCompactionResponse(t, req, compactionSummary)
+		}
 		if !req.Stream {
-			if strings.Contains(body, "You are performing a context compaction") {
-				return chattest.AnthropicNonStreamingResponse(compactionSummary)
-			}
 			return chattest.AnthropicNonStreamingResponse("AI Gateway Compaction")
 		}
 
@@ -5398,10 +5401,10 @@ func TestActiveServer_CompactionRecordsMetric(t *testing.T) {
 	var streamCount atomic.Int32
 	anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 		body := anthropicRequestBody(t, *req)
+		if strings.Contains(body, "You are performing a context compaction") {
+			return anthropicCompactionResponse(t, req, compactionSummary)
+		}
 		if !req.Stream {
-			if strings.Contains(body, "You are performing a context compaction") {
-				return anthropicCompactionResponse(compactionSummary)
-			}
 			return chattest.AnthropicNonStreamingResponse("title")
 		}
 		switch streamCount.Add(1) {
@@ -5490,12 +5493,12 @@ func TestActiveServer_Compaction(t *testing.T) {
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			requests.record(req)
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				require.Contains(t, body, "read_file")
+				require.Contains(t, body, "package main")
+				return anthropicCompactionResponse(t, req, compactionSummary)
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					require.Contains(t, body, "read_file")
-					require.Contains(t, body, "package main")
-					return anthropicCompactionResponse(compactionSummary)
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			switch streamCount.Add(1) {
@@ -5586,7 +5589,7 @@ func TestActiveServer_Compaction(t *testing.T) {
 			body := anthropicRequestBody(t, *req)
 			if strings.Contains(body, "You are performing a context compaction") {
 				compactionRequests.Add(1)
-				return anthropicCompactionResponse(compactionSummary)
+				return anthropicCompactionResponse(t, req, compactionSummary)
 			}
 			if !req.Stream {
 				return chattest.AnthropicNonStreamingResponse("title")
@@ -5625,10 +5628,10 @@ func TestActiveServer_Compaction(t *testing.T) {
 		var streamCount atomic.Int32
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				return anthropicCompactionResponse(t, req, compactionSummary)
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					return anthropicCompactionResponse(compactionSummary)
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			switch streamCount.Add(1) {
@@ -5727,13 +5730,13 @@ func TestActiveServer_ManualCompaction(t *testing.T) {
 		var compactionRequests atomic.Int32
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				compactionRequests.Add(1)
+				require.Contains(t, body, "hello from the user")
+				require.True(t, anthropicMessageHasEphemeralCacheControl(t, req.Messages[len(req.Messages)-1]))
+				return anthropicCompactionResponse(t, req, compactionSummary)
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					compactionRequests.Add(1)
-					require.Contains(t, body, "hello from the user")
-					require.True(t, anthropicMessageHasEphemeralCacheControl(t, req.Messages[len(req.Messages)-1]))
-					return anthropicCompactionResponse(compactionSummary)
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			streamCount.Add(1)
@@ -5819,11 +5822,11 @@ func TestActiveServer_ManualCompaction(t *testing.T) {
 		var compactionRequests atomic.Int32
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				compactionRequests.Add(1)
+				return anthropicCompactionResponse(t, req, compactionSummary)
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					compactionRequests.Add(1)
-					return anthropicCompactionResponse(compactionSummary)
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			return chattest.AnthropicStreamingResponse(chattest.AnthropicTextChunks("assistant answer")...)
@@ -5879,22 +5882,22 @@ func TestActiveServer_ManualCompaction(t *testing.T) {
 		var compactionToolCounts []int
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
-			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					mu.Lock()
-					compactionToolCounts = append(compactionToolCounts, len(req.Tools))
-					mu.Unlock()
-					// The tool definitions push the summary request past
-					// the window that the tool-less request still fits.
-					if len(req.Tools) > 0 {
-						return chattest.AnthropicResponse{Error: &chattest.ErrorResponse{
-							StatusCode: http.StatusBadRequest,
-							Type:       "invalid_request_error",
-							Message:    "prompt is too long: 20000 tokens > 16385 maximum",
-						}}
-					}
-					return anthropicCompactionResponse(compactionSummary)
+			if strings.Contains(body, "You are performing a context compaction") {
+				mu.Lock()
+				compactionToolCounts = append(compactionToolCounts, len(req.Tools))
+				mu.Unlock()
+				// The tool definitions push the summary request past
+				// the window that the tool-less request still fits.
+				if len(req.Tools) > 0 {
+					return chattest.AnthropicResponse{Error: &chattest.ErrorResponse{
+						StatusCode: http.StatusBadRequest,
+						Type:       "invalid_request_error",
+						Message:    "prompt is too long: 20000 tokens > 16385 maximum",
+					}}
 				}
+				return anthropicCompactionResponse(t, req, compactionSummary)
+			}
+			if !req.Stream {
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			return chattest.AnthropicStreamingResponse(chattest.AnthropicTextChunks("assistant answer")...)
@@ -6119,11 +6122,11 @@ func TestActiveServer_ManualClear(t *testing.T) {
 		var compactionRequests atomic.Int32
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				compactionRequests.Add(1)
+				return anthropicCompactionResponse(t, req, "unexpected summary")
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					compactionRequests.Add(1)
-					return anthropicCompactionResponse("unexpected summary")
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			// The first turn exceeds the threshold, so stale usage would
@@ -6169,10 +6172,10 @@ func TestActiveServer_ManualClear(t *testing.T) {
 		db, ps := dbtestutil.NewDB(t)
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				return anthropicCompactionResponse(t, req, "compaction summary")
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					return anthropicCompactionResponse("compaction summary")
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			return chattest.AnthropicStreamingResponse(chattest.AnthropicTextChunks("assistant answer")...)
@@ -6394,14 +6397,17 @@ func TestActiveServer_CompactionModelOverride(t *testing.T) {
 			},
 		},
 		{
-			// 3276 is 0.8 (high) of the summary call's default 4096 max_tokens.
+			// High effort maps to 0.8 of the summary call's max_tokens
+			// (the remaining-window clamp; its exact value is pinned in
+			// the chatloop unit tests).
 			name:          "legacy budget-thinking override model",
 			overrideModel: "claude-haiku-4-5",
 			effort:        "high",
 			assertSummaryRequest: func(t *testing.T, req *chattest.AnthropicRequest) {
 				require.Empty(t, string(req.OutputConfig))
 				require.Contains(t, string(req.Thinking), `"type":"enabled"`)
-				require.Contains(t, string(req.Thinking), `"budget_tokens":3276`)
+				wantBudget := int64(float64(req.MaxTokens) * 0.8)
+				require.Contains(t, string(req.Thinking), fmt.Sprintf(`"budget_tokens":%d`, wantBudget))
 			},
 		},
 		{
@@ -6434,23 +6440,27 @@ func TestActiveServer_CompactionModelOverride(t *testing.T) {
 			var streamCount atomic.Int32
 			anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 				body := anthropicRequestBody(t, *req)
-				if !req.Stream {
-					if strings.Contains(body, "You are performing a context compaction") {
-						require.Equal(t, tc.overrideModel, req.Model)
-						if tc.keepsTools {
-							require.NotEmpty(t, req.Tools)
-						} else {
-							require.Empty(t, req.Tools, "a different model shares no prompt cache, so the summary carries no tool definitions")
-						}
-						tc.assertSummaryRequest(t, req)
-						return anthropicCompactionResponse(compactionSummary)
+				if strings.Contains(body, "You are performing a context compaction") {
+					require.Equal(t, tc.overrideModel, req.Model)
+					if tc.keepsTools {
+						require.NotEmpty(t, req.Tools)
+					} else {
+						require.Empty(t, req.Tools, "a different model shares no prompt cache, so the summary carries no tool definitions")
 					}
+					tc.assertSummaryRequest(t, req)
+					return anthropicCompactionResponse(t, req, compactionSummary)
+				}
+				if !req.Stream {
 					return chattest.AnthropicNonStreamingResponse("title")
 				}
 				require.Equal(t, chatModelName, req.Model)
 				switch streamCount.Add(1) {
 				case 1:
-					return highUsageReadFileResponse("/tmp/a.txt")
+					// A large window keeps the summary cap clamp
+					// (limit minus usage and reserves) above the
+					// minimum legacy thinking budget so the effort
+					// mapping stays observable on the summary request.
+					return readFileResponseWithInputTokens("/tmp/a.txt", 80_000)
 				default:
 					require.Contains(t, body, compactionSummary)
 					require.Empty(t, string(req.OutputConfig),
@@ -6464,7 +6474,7 @@ func TestActiveServer_CompactionModelOverride(t *testing.T) {
 				}
 			})
 			user, org, model := seedAnthropicChatDependencies(t, db, anthropicURL)
-			model = updateChatModelCompressionThreshold(t, db, model, 100, thresholdPercent)
+			model = updateChatModelCompressionThreshold(t, db, model, 100_000, thresholdPercent)
 			overrideModel := seedOverrideModel(ctx, t, db, model, tc.overrideModel, tc.effort, 1_000_000)
 			ws, dbAgent := seedWorkspaceWithAgent(t, db, user.ID)
 
@@ -6548,11 +6558,11 @@ func TestActiveServer_CompactionModelOverride(t *testing.T) {
 		var streamCount atomic.Int32
 		anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 			body := anthropicRequestBody(t, *req)
+			if strings.Contains(body, "You are performing a context compaction") {
+				require.Equal(t, overrideModelName, req.Model)
+				return anthropicCompactionResponse(t, req, compactionSummary)
+			}
 			if !req.Stream {
-				if strings.Contains(body, "You are performing a context compaction") {
-					require.Equal(t, overrideModelName, req.Model)
-					return anthropicCompactionResponse(compactionSummary)
-				}
 				return chattest.AnthropicNonStreamingResponse("title")
 			}
 			switch streamCount.Add(1) {
@@ -11775,10 +11785,10 @@ func TestActiveServer_ChatTurnDebugRunRecordsMCPConnectOnDecisionError(t *testin
 	// terminally with the still-over-limit error.
 	var streamCount atomic.Int32
 	anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
+		if strings.Contains(anthropicRequestBody(t, *req), "You are performing a context compaction") {
+			return anthropicCompactionResponse(t, req, "summary text for compaction")
+		}
 		if !req.Stream {
-			if strings.Contains(anthropicRequestBody(t, *req), "You are performing a context compaction") {
-				return anthropicCompactionResponse("summary text for compaction")
-			}
 			return chattest.AnthropicNonStreamingResponse("title")
 		}
 		if streamCount.Add(1) == 1 {
diff --git a/coderd/x/chatd/chatloop/chatloop.go b/coderd/x/chatd/chatloop/chatloop.go
index 2d955dc201..8f656b4e86 100644
--- a/coderd/x/chatd/chatloop/chatloop.go
+++ b/coderd/x/chatd/chatloop/chatloop.go
@@ -232,6 +232,10 @@ type GenerateCompactionOptions struct {
 	// Clock measures the summary call duration. Required.
 	Clock quartz.Clock
 
+	// StreamSilenceTimeout bounds how long the summary stream may go
+	// without yielding a part. Defaults to defaultStreamSilenceTimeout.
+	StreamSilenceTimeout time.Duration
+
 	// OnModelStreamStart runs immediately before the summary model call,
 	// at the instant CompactionResult.Runtime starts measuring.
 	OnModelStreamStart func()
diff --git a/coderd/x/chatd/chatloop/compaction.go b/coderd/x/chatd/chatloop/compaction.go
index 2d3dd559b2..9c9e568e3a 100644
--- a/coderd/x/chatd/chatloop/compaction.go
+++ b/coderd/x/chatd/chatloop/compaction.go
@@ -14,6 +14,7 @@ import (
 
 	"github.com/coder/coder/v2/coderd/x/chatd/chatdebug"
 	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/quartz"
 )
 
 const (
@@ -102,6 +103,12 @@ type CompactionOptions struct {
 	// summary call uses the exact same ordered definitions.
 	ToolDefinitions []fantasy.Tool
 
+	// Clock and StreamSilenceTimeout guard the summary stream against a
+	// provider that opens the stream but stops yielding parts. Zero values
+	// fall back to a real clock and DefaultStreamSilenceTimeout.
+	Clock                quartz.Clock
+	StreamSilenceTimeout time.Duration
+
 	// Force skips the threshold gate (including the threshold=100
 	// disable and the zero-usage early return). Set for manual,
 	// user-requested compactions.
@@ -171,6 +178,24 @@ func GenerateCompaction(ctx context.Context, opts GenerateCompactionOptions) (Co
 		return CompactionResult{}, nil
 	}
 
+	// Sum-enforcing providers reject requests whose input plus
+	// max_tokens exceeds the context window, so bound the summary cap
+	// by the remaining window. contextTokens covers only the trigger
+	// step's prompt, so also reserve that step's output, the tool
+	// results executed after it, and the summary prompt appended by
+	// generateCompactionSummary, all of which become input to the
+	// summary request. Degenerate cases (unknown limit, no room left)
+	// leave the cap unchanged.
+	if config.SummaryCall.MaxOutputTokens != nil {
+		promptBytes := len(config.SummaryPrompt) + len(config.SummaryHint)
+		promptTokens := int64((promptBytes + bytesPerTokenEstimate - 1) / bytesPerTokenEstimate)
+		reserved := opts.StepUsage.OutputTokens + promptTokens + trailingToolResultTokens(opts.Messages)
+		remaining := contextLimit - contextTokens - reserved
+		if remaining > 0 && remaining < *config.SummaryCall.MaxOutputTokens {
+			config.SummaryCall.MaxOutputTokens = &remaining
+		}
+	}
+
 	if config.PublishMessagePart != nil && config.ToolCallID != "" {
 		config.PublishMessagePart(
 			codersdk.ChatMessageRoleAssistant,
@@ -226,24 +251,26 @@ func GenerateCompaction(ctx context.Context, opts GenerateCompactionOptions) (Co
 
 func normalizedCompactionGenerateConfig(opts GenerateCompactionOptions) (CompactionOptions, bool) {
 	config := CompactionOptions{
-		ThresholdPercent:    opts.ThresholdPercent,
-		ContextLimit:        opts.ContextLimit,
-		SummaryPrompt:       opts.SummaryPrompt,
-		SummaryHint:         opts.SummaryHint,
-		SystemSummaryPrefix: opts.SystemSummaryPrefix,
-		DebugSvc:            opts.DebugSvc,
-		ChatID:              opts.ChatID,
-		HistoryTipMessageID: opts.HistoryTipMessageID,
-		ResolvedProvider:    opts.ResolvedProvider,
-		ResolvedModel:       opts.ResolvedModel,
-		ModelConfigID:       opts.ModelConfigID,
-		SummaryCall:         opts.SummaryCall,
-		ToolDefinitions:     opts.ToolDefinitions,
-		Force:               opts.Force,
-		Source:              opts.Source,
-		ToolCallID:          opts.ToolCallID,
-		ToolName:            opts.ToolName,
-		PublishMessagePart:  opts.PublishMessagePart,
+		ThresholdPercent:     opts.ThresholdPercent,
+		ContextLimit:         opts.ContextLimit,
+		SummaryPrompt:        opts.SummaryPrompt,
+		SummaryHint:          opts.SummaryHint,
+		SystemSummaryPrefix:  opts.SystemSummaryPrefix,
+		DebugSvc:             opts.DebugSvc,
+		ChatID:               opts.ChatID,
+		HistoryTipMessageID:  opts.HistoryTipMessageID,
+		ResolvedProvider:     opts.ResolvedProvider,
+		ResolvedModel:        opts.ResolvedModel,
+		ModelConfigID:        opts.ModelConfigID,
+		SummaryCall:          opts.SummaryCall,
+		ToolDefinitions:      opts.ToolDefinitions,
+		Force:                opts.Force,
+		Source:               opts.Source,
+		ToolCallID:           opts.ToolCallID,
+		ToolName:             opts.ToolName,
+		PublishMessagePart:   opts.PublishMessagePart,
+		Clock:                opts.Clock,
+		StreamSilenceTimeout: opts.StreamSilenceTimeout,
 	}
 	if strings.TrimSpace(config.SummaryPrompt) == "" {
 		config.SummaryPrompt = defaultCompactionSummaryPrompt
@@ -281,6 +308,37 @@ func publishCompactionError(config CompactionOptions, msg string) {
 	)
 }
 
+// trailingToolResultTokens estimates tokens for the tool-result
+// messages that follow the usage-measured assistant step. Local tools
+// execute before compaction, so their results are input to the summary
+// request but absent from StepUsage.
+func trailingToolResultTokens(messages []fantasy.Message) int64 {
+	totalBytes := 0
+	for i := len(messages) - 1; i >= 0 && messages[i].Role == fantasy.MessageRoleTool; i-- {
+		for _, part := range messages[i].Content {
+			result, ok := part.(fantasy.ToolResultPart)
+			if !ok {
+				resultPtr, okPtr := part.(*fantasy.ToolResultPart)
+				if !okPtr || resultPtr == nil {
+					continue
+				}
+				result = *resultPtr
+			}
+			switch output := result.Output.(type) {
+			case fantasy.ToolResultOutputContentText:
+				totalBytes += len(output.Text)
+			case fantasy.ToolResultOutputContentError:
+				if output.Error != nil {
+					totalBytes += len(output.Error.Error())
+				}
+			case fantasy.ToolResultOutputContentMedia:
+				totalBytes += len(output.Data) + len(output.Text)
+			}
+		}
+	}
+	return int64((totalBytes + bytesPerTokenEstimate - 1) / bytesPerTokenEstimate)
+}
+
 // contextTokensFromUsage returns the total context token count from
 // a step's usage report. It sums input, cache-read, and
 // cache-creation tokens when available, falling back to TotalTokens
@@ -442,7 +500,7 @@ func generateCompactionSummary(
 
 	summaryCtx, finishDebugRun := startCompactionDebugRun(ctx, options)
 	defer func() {
-		// If model.Generate (or anything else below) panics, the
+		// If model.Stream (or anything else below) panics, the
 		// named err return is still nil at this point. Without the
 		// recover hook we would finalize the debug run as Completed
 		// in the exact crash path operators rely on to diagnose
@@ -459,33 +517,116 @@ func generateCompactionSummary(
 	call := options.SummaryCall
 	call.Prompt = summaryPrompt
 	call.Tools = options.ToolDefinitions
-	response, err := model.Generate(summaryCtx, call)
+	clock := options.Clock
+	if clock == nil {
+		clock = quartz.NewReal()
+	}
+	timeout := options.StreamSilenceTimeout
+	if timeout == 0 {
+		timeout = DefaultStreamSilenceTimeout
+	}
+	// NopMetrics: TTFT is an assistant-generation metric, so the summary
+	// stream must not record into it.
+	streamSummaryText := func() (string, error) {
+		attempt, err := guardedStream(
+			summaryCtx,
+			options.ResolvedProvider,
+			options.ResolvedModel,
+			clock,
+			timeout,
+			func(attemptCtx context.Context) (fantasy.StreamResponse, error) {
+				return model.Stream(attemptCtx, call)
+			},
+			NopMetrics(),
+		)
+		if err != nil {
+			return "", xerrors.Errorf("stream summary text: %w", wrapProviderStreamError(options.ResolvedProvider, err))
+		}
+		defer attempt.release()
+
+		textPartIndexes := make(map[string]int)
+		textParts := make([]string, 0, 1)
+		var (
+			reasoningSeen bool
+			finishSeen    bool
+			finishReason  fantasy.FinishReason
+			streamErr     error
+		)
+		for part := range attempt.stream {
+			switch part.Type {
+			case fantasy.StreamPartTypeTextStart:
+				if _, ok := textPartIndexes[part.ID]; ok {
+					continue
+				}
+				textPartIndexes[part.ID] = len(textParts)
+				textParts = append(textParts, part.Delta)
+			case fantasy.StreamPartTypeTextDelta:
+				index, ok := textPartIndexes[part.ID]
+				if !ok {
+					index = len(textParts)
+					textPartIndexes[part.ID] = index
+					textParts = append(textParts, "")
+				}
+				textParts[index] += part.Delta
+			case fantasy.StreamPartTypeReasoningStart,
+				fantasy.StreamPartTypeReasoningDelta,
+				fantasy.StreamPartTypeReasoningEnd:
+				reasoningSeen = true
+			case fantasy.StreamPartTypeFinish:
+				finishSeen = true
+				finishReason = part.FinishReason
+			case fantasy.StreamPartTypeError:
+				streamErr = part.Error
+				if streamErr == nil {
+					streamErr = xerrors.New("model returned an error part")
+				}
+			}
+			if streamErr != nil {
+				break
+			}
+		}
+		if err := attempt.finish(streamErr); err != nil {
+			// Providers can surface remote stream resets as bare
+			// context.Canceled; wrap them like GenerateAssistant so the
+			// generation loop retries instead of terminally erroring.
+			return "", xerrors.Errorf("stream summary text: %w", wrapProviderStreamError(options.ResolvedProvider, err))
+		}
+		if !finishSeen {
+			// A stream that ends without a finish part was interrupted.
+			// Committing its partial text would compact history against an
+			// incomplete summary.
+			if ctxErr := summaryCtx.Err(); ctxErr != nil {
+				return "", xerrors.Errorf("stream summary text: %w", ctxErr)
+			}
+			return "", xerrors.New("compaction summary stream ended without a finish part")
+		}
+
+		parts := make([]string, 0, len(textParts))
+		for _, text := range textParts {
+			text = strings.TrimSpace(text)
+			if text != "" {
+				parts = append(parts, text)
+			}
+		}
+		joined := strings.TrimSpace(strings.Join(parts, " "))
+		if joined == "" && (finishReason == fantasy.FinishReasonLength || reasoningSeen) {
+			return "", xerrors.New("compaction summary was truncated at the output token cap")
+		}
+		return joined, nil
+	}
+	summary, err = streamSummaryText()
 	if err != nil && len(call.Tools) > 0 && isContextTooLargeError(err) {
 		// Tool definitions keep the summary request on the parent turn's
 		// cacheable prefix, but they also make it larger than the turn
 		// that just overflowed. Compaction is the recovery path for an
 		// over-limit conversation, so fall back to the tool-less request,
-		// which still fits whenever the history alone does.
+		// which still fits whenever the history alone does. The rejection
+		// can arrive from the stream open or as an in-stream error part,
+		// so the retry wraps the whole attempt.
 		call.Tools = nil
-		response, err = model.Generate(summaryCtx, call)
+		summary, err = streamSummaryText()
 	}
-	if err != nil {
-		return "", xerrors.Errorf("generate summary text: %w", err)
-	}
-
-	parts := make([]string, 0, len(response.Content))
-	for _, block := range response.Content {
-		textBlock, ok := fantasy.AsContentType[fantasy.TextContent](block)
-		if !ok {
-			continue
-		}
-		text := strings.TrimSpace(textBlock.Text)
-		if text == "" {
-			continue
-		}
-		parts = append(parts, text)
-	}
-	return strings.TrimSpace(strings.Join(parts, " ")), nil
+	return summary, err
 }
 
 // contextTooLargePhrases are context-window rejections fantasy does not
diff --git a/coderd/x/chatd/chatloop/compaction_internal_test.go b/coderd/x/chatd/chatloop/compaction_internal_test.go
index 14e501b4cb..77debd7ff7 100644
--- a/coderd/x/chatd/chatloop/compaction_internal_test.go
+++ b/coderd/x/chatd/chatloop/compaction_internal_test.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"encoding/json"
 	"net/http"
+	"strings"
 	"testing"
 	"time"
 
@@ -19,12 +20,32 @@ import (
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbmock"
 	"github.com/coder/coder/v2/coderd/x/chatd/chatdebug"
+	"github.com/coder/coder/v2/coderd/x/chatd/chaterror"
 	"github.com/coder/coder/v2/coderd/x/chatd/chattest"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/testutil"
 	"github.com/coder/quartz"
 )
 
+func compactionStream(parts ...fantasy.StreamPart) fantasy.StreamResponse {
+	return func(yield func(fantasy.StreamPart) bool) {
+		for _, part := range parts {
+			if !yield(part) {
+				return
+			}
+		}
+	}
+}
+
+func summaryTextStream() fantasy.StreamResponse {
+	return compactionStream(
+		fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+		fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "summary"},
+		fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"},
+		fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+	)
+}
+
 func TestStartCompactionDebugRun_DoesNotReportDebugErrors(t *testing.T) {
 	t.Parallel()
 
@@ -184,7 +205,7 @@ func TestGenerateCompactionSummary_PanicFinalizesAsError(t *testing.T) {
 
 	model := &chattest.FakeModel{
 		ProviderName: "fake",
-		GenerateFn: func(_ context.Context, _ fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
 			panic("compaction model crash")
 		},
 	}
@@ -245,9 +266,9 @@ func TestGenerateCompactionSummaryPreservesCallOptions(t *testing.T) {
 	model := &chattest.FakeModel{
 		ProviderName: "fake",
 		ModelName:    "fake-model",
-		GenerateFn: func(_ context.Context, call fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(_ context.Context, call fantasy.Call) (fantasy.StreamResponse, error) {
 			got = call
-			return &fantasy.Response{Content: []fantasy.Content{fantasy.TextContent{Text: "summary"}}}, nil
+			return summaryTextStream(), nil
 		},
 	}
 
@@ -301,9 +322,9 @@ func TestGenerateCompactionSummaryUsesToolDefinitions(t *testing.T) {
 	model := &chattest.FakeModel{
 		ProviderName: "fake",
 		ModelName:    "fake-model",
-		GenerateFn: func(_ context.Context, call fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(_ context.Context, call fantasy.Call) (fantasy.StreamResponse, error) {
 			got = call
-			return &fantasy.Response{Content: []fantasy.Content{fantasy.TextContent{Text: "summary"}}}, nil
+			return summaryTextStream(), nil
 		},
 	}
 
@@ -335,9 +356,9 @@ func TestGenerateCompactionSummaryAppliesAnthropicPromptCaching(t *testing.T) {
 	model := &chattest.FakeModel{
 		ProviderName: fantasyanthropic.Name,
 		ModelName:    "claude",
-		GenerateFn: func(_ context.Context, call fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(_ context.Context, call fantasy.Call) (fantasy.StreamResponse, error) {
 			got = call
-			return &fantasy.Response{Content: []fantasy.Content{fantasy.TextContent{Text: "summary"}}}, nil
+			return summaryTextStream(), nil
 		},
 	}
 
@@ -370,7 +391,7 @@ func TestGenerateCompactionSummaryRetriesWithoutToolsWhenContextTooLarge(t *test
 	model := &chattest.FakeModel{
 		ProviderName: "fake",
 		ModelName:    "fake-model",
-		GenerateFn: func(_ context.Context, call fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(_ context.Context, call fantasy.Call) (fantasy.StreamResponse, error) {
 			calls = append(calls, call)
 			if len(call.Tools) > 0 {
 				return nil, &fantasy.ProviderError{
@@ -379,7 +400,7 @@ func TestGenerateCompactionSummaryRetriesWithoutToolsWhenContextTooLarge(t *test
 					StatusCode: http.StatusBadRequest,
 				}
 			}
-			return &fantasy.Response{Content: []fantasy.Content{fantasy.TextContent{Text: "summary"}}}, nil
+			return summaryTextStream(), nil
 		},
 	}
 
@@ -446,7 +467,7 @@ func TestGenerateCompactionSummaryDoesNotRetryOtherFailures(t *testing.T) {
 			model := &chattest.FakeModel{
 				ProviderName: "fake",
 				ModelName:    "fake-model",
-				GenerateFn: func(_ context.Context, _ fantasy.Call) (*fantasy.Response, error) {
+				StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
 					calls++
 					return nil, tc.err
 				},
@@ -564,16 +585,21 @@ func TestGenerateCompactionSummary_UsesCallerContext(t *testing.T) {
 
 	type contextKey string
 	testCtx := context.WithValue(context.Background(), contextKey("key"), "value")
-	var ctxSeen context.Context
+	var (
+		ctxSeen   context.Context
+		errAtCall error
+	)
 	model := &chattest.FakeModel{
 		ProviderName: "fake",
-		GenerateFn: func(ctx context.Context, _ fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(ctx context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
 			ctxSeen = ctx
-			return &fantasy.Response{
-				Content: []fantasy.Content{
-					fantasy.TextContent{Text: "summary"},
-				},
-			}, nil
+			errAtCall = ctx.Err()
+			return compactionStream(
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "summary"},
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"},
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+			), nil
 		},
 	}
 
@@ -583,13 +609,161 @@ func TestGenerateCompactionSummary_UsesCallerContext(t *testing.T) {
 	)
 	require.NoError(t, err)
 	require.Equal(t, "summary", summary)
-	require.Same(t, testCtx, ctxSeen)
-	require.NoError(t, ctxSeen.Err())
+	// The silence guard wraps the caller context in a cancelable child that
+	// is released after the summary completes, so assert inheritance rather
+	// than identity: values propagate, the context is live at call time, and
+	// no deadline is attached (the guard uses a timer, not a context
+	// deadline).
+	require.NoError(t, errAtCall)
 	_, ok := ctxSeen.Deadline()
 	require.False(t, ok)
 	require.Equal(t, "value", ctxSeen.Value(contextKey("key")))
 }
 
+func TestGenerateCompactionSummary_Stream(t *testing.T) {
+	t.Parallel()
+
+	t.Run("joins text blocks", func(t *testing.T) {
+		t.Parallel()
+
+		model := &chattest.FakeModel{
+			ProviderName: "fake",
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return compactionStream(
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "first"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "first", Delta: " first "},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "first"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "second"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "second", Delta: " second "},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "second"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+				), nil
+			},
+		}
+
+		summary, err := generateCompactionSummary(context.Background(), model, nil, CompactionOptions{})
+		require.NoError(t, err)
+		require.Equal(t, "first second", summary)
+	})
+
+	t.Run("reports output cap truncation", func(t *testing.T) {
+		t.Parallel()
+
+		model := &chattest.FakeModel{
+			ProviderName: "fake",
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return compactionStream(
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeReasoningStart, ID: "reasoning"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeReasoningDelta, ID: "reasoning", Delta: "thinking"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeReasoningEnd, ID: "reasoning"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonLength},
+				), nil
+			},
+		}
+
+		summary, err := generateCompactionSummary(context.Background(), model, nil, CompactionOptions{})
+		require.Empty(t, summary)
+		require.EqualError(t, err, "compaction summary was truncated at the output token cap")
+	})
+
+	t.Run("rejects stream without finish part", func(t *testing.T) {
+		t.Parallel()
+
+		model := &chattest.FakeModel{
+			ProviderName: "fake",
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return compactionStream(
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "partial summary"},
+				), nil
+			},
+		}
+
+		summary, err := generateCompactionSummary(context.Background(), model, nil, CompactionOptions{})
+		require.Empty(t, summary)
+		require.EqualError(t, err, "compaction summary stream ended without a finish part")
+	})
+
+	t.Run("classifies canceled stream open as transport reset", func(t *testing.T) {
+		t.Parallel()
+
+		model := &chattest.FakeModel{
+			ProviderName: "fake",
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return nil, context.Canceled
+			},
+		}
+
+		summary, err := generateCompactionSummary(context.Background(), model, nil, CompactionOptions{
+			ResolvedProvider: "fake",
+		})
+		require.Empty(t, summary)
+		require.ErrorIs(t, err, chaterror.ErrProviderTransportReset)
+		classified := chaterror.Classify(err)
+		require.True(t, classified.Retryable)
+		require.Equal(t, "fake", classified.Provider)
+	})
+
+	t.Run("classifies canceled error part as transport reset", func(t *testing.T) {
+		t.Parallel()
+
+		model := &chattest.FakeModel{
+			ProviderName: "fake",
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return compactionStream(
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeError, Error: context.Canceled},
+				), nil
+			},
+		}
+
+		summary, err := generateCompactionSummary(context.Background(), model, nil, CompactionOptions{
+			ResolvedProvider: "fake",
+		})
+		require.Empty(t, summary)
+		require.ErrorIs(t, err, chaterror.ErrProviderTransportReset)
+		classified := chaterror.Classify(err)
+		require.True(t, classified.Retryable)
+		require.Equal(t, "fake", classified.Provider)
+	})
+
+	t.Run("classifies stream silence", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		clock := quartz.NewMock(t)
+		trap := clock.Trap().AfterFunc(streamSilenceGuardTimerTag)
+		defer trap.Close()
+		model := &chattest.FakeModel{
+			ProviderName: "openai",
+			StreamFn: func(ctx context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return func(yield func(fantasy.StreamPart) bool) {
+					<-ctx.Done()
+				}, nil
+			},
+		}
+
+		done := make(chan error, 1)
+		go func() {
+			_, err := generateCompactionSummary(context.Background(), model, nil, CompactionOptions{
+				ResolvedProvider:     "openai",
+				Clock:                clock,
+				StreamSilenceTimeout: 5 * time.Millisecond,
+			})
+			done <- err
+		}()
+
+		trap.MustWait(ctx).MustRelease(ctx)
+		_, waiter := clock.AdvanceNext()
+		waiter.MustWait(ctx)
+		err := <-done
+		require.Error(t, err)
+		classified := chaterror.Classify(err)
+		require.Equal(t, codersdk.ChatErrorKindStreamSilenceTimeout, classified.Kind)
+		require.Equal(t, "openai", classified.Provider)
+		require.True(t, classified.Retryable)
+	})
+}
+
 // TestGenerateCompaction_ForceBypassesThresholdGates verifies the
 // manual-compaction contract: Force runs the summary even when usage
 // is below threshold, when usage is zero, and when threshold=100
@@ -602,13 +776,14 @@ func TestGenerateCompaction_ForceBypassesThresholdGates(t *testing.T) {
 		return &chattest.FakeModel{
 			ProviderName: "fake",
 			ModelName:    "fake-model",
-			GenerateFn: func(_ context.Context, _ fantasy.Call) (*fantasy.Response, error) {
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
 				*calls++
-				return &fantasy.Response{
-					Content: []fantasy.Content{
-						fantasy.TextContent{Text: "forced summary"},
-					},
-				}, nil
+				return compactionStream(
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "forced summary"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"},
+					fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+				), nil
 			},
 		}
 	}
@@ -670,6 +845,77 @@ func TestGenerateCompaction_ForceBypassesThresholdGates(t *testing.T) {
 	}
 }
 
+// TestGenerateCompaction_ClampsSummaryCapToRemainingWindow pins the
+// summary output cap bound: sum-enforcing providers reject requests
+// whose input plus max_tokens exceeds the context window, so the cap
+// shrinks to the remaining window minus the trigger step's output and
+// the appended summary prompt (ceil(bytes/3) tokens), and degenerate
+// cases stay unchanged.
+func TestGenerateCompaction_ClampsSummaryCapToRemainingWindow(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		name            string
+		contextLimit    int64
+		inputTokens     int64
+		outputTokens    int64
+		toolResultBytes int
+		cap             int64
+		wantCap         int64
+	}{
+		{name: "clamps to remaining window", contextLimit: 100, inputTokens: 75, outputTokens: 10, cap: 64_000, wantCap: 13},
+		{name: "reserves trailing tool results", contextLimit: 100, inputTokens: 72, toolResultBytes: 30, cap: 64_000, wantCap: 16},
+		{name: "keeps cap that fits", contextLimit: 200_000, inputTokens: 140_000, outputTokens: 500, cap: 50_000, wantCap: 50_000},
+		{name: "usage at limit leaves cap unchanged", contextLimit: 100, inputTokens: 100, cap: 64_000, wantCap: 64_000},
+		{name: "reserves leave no room, cap unchanged", contextLimit: 100, inputTokens: 80, outputTokens: 25, cap: 64_000, wantCap: 64_000},
+	}
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			var gotCap *int64
+			model := &chattest.FakeModel{
+				ProviderName: "fake",
+				ModelName:    "fake-model",
+				StreamFn: func(_ context.Context, call fantasy.Call) (fantasy.StreamResponse, error) {
+					gotCap = call.MaxOutputTokens
+					return compactionStream(
+						fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+						fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "summary"},
+						fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"},
+						fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+					), nil
+				},
+			}
+			capTokens := tc.cap
+			messages := []fantasy.Message{textMessage(fantasy.MessageRoleUser, "hello")}
+			if tc.toolResultBytes > 0 {
+				messages = append(messages, fantasy.Message{
+					Role: fantasy.MessageRoleTool,
+					Content: []fantasy.MessagePart{fantasy.ToolResultPart{
+						ToolCallID: "call-1",
+						Output:     fantasy.ToolResultOutputContentText{Text: strings.Repeat("x", tc.toolResultBytes)},
+					}},
+				})
+			}
+			result, err := GenerateCompaction(context.Background(), GenerateCompactionOptions{
+				Model:            model,
+				Messages:         messages,
+				Clock:            quartz.NewMock(t),
+				ThresholdPercent: 70,
+				ContextLimit:     tc.contextLimit,
+				SummaryPrompt:    "prompt",
+				StepUsage:        fantasy.Usage{InputTokens: tc.inputTokens, OutputTokens: tc.outputTokens},
+				SummaryCall:      fantasy.Call{MaxOutputTokens: &capTokens},
+			})
+			require.NoError(t, err)
+			require.Equal(t, "summary", result.SummaryReport)
+			require.NotNil(t, gotCap)
+			require.Equal(t, tc.wantCap, *gotCap)
+		})
+	}
+}
+
 // TestGenerateCompaction_DefaultSourceAutomatic verifies an unforced
 // over-threshold run reports the automatic source by default.
 func TestGenerateCompaction_DefaultSourceAutomatic(t *testing.T) {
@@ -678,12 +924,13 @@ func TestGenerateCompaction_DefaultSourceAutomatic(t *testing.T) {
 	model := &chattest.FakeModel{
 		ProviderName: "fake",
 		ModelName:    "fake-model",
-		GenerateFn: func(_ context.Context, _ fantasy.Call) (*fantasy.Response, error) {
-			return &fantasy.Response{
-				Content: []fantasy.Content{
-					fantasy.TextContent{Text: "auto summary"},
-				},
-			}, nil
+		StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+			return compactionStream(
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "auto summary"},
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"},
+				fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+			), nil
 		},
 	}
 	result, err := GenerateCompaction(context.Background(), GenerateCompactionOptions{
@@ -707,11 +954,13 @@ func TestGenerateCompaction_SummaryEstimate(t *testing.T) {
 			var parts []codersdk.ChatMessagePart
 			result, err := GenerateCompaction(t.Context(), GenerateCompactionOptions{
 				Model: &chattest.FakeModel{
-					GenerateFn: func(context.Context, fantasy.Call) (*fantasy.Response, error) {
-						return &fantasy.Response{
-							Content: []fantasy.Content{fantasy.TextContent{Text: "界x"}},
-							Usage:   fantasy.Usage{InputTokens: 900, OutputTokens: 400},
-						}, nil
+					StreamFn: func(context.Context, fantasy.Call) (fantasy.StreamResponse, error) {
+						return compactionStream(
+							fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"},
+							fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "界x"},
+							fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"},
+							fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop},
+						), nil
 					},
 				},
 				Messages:            []fantasy.Message{textMessage(fantasy.MessageRoleUser, "hello")},
diff --git a/coderd/x/chatd/chatloop/runtime_test.go b/coderd/x/chatd/chatloop/runtime_test.go
index 722eaf06b3..5ac714b080 100644
--- a/coderd/x/chatd/chatloop/runtime_test.go
+++ b/coderd/x/chatd/chatloop/runtime_test.go
@@ -130,12 +130,13 @@ func TestGenerateCompaction_RecordsRuntime(t *testing.T) {
 	model := &chattest.FakeModel{
 		ProviderName: "test-provider",
 		ModelName:    "test-model",
-		GenerateFn: func(_ context.Context, _ fantasy.Call) (*fantasy.Response, error) {
+		StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
 			clock.Advance(1500 * time.Millisecond)
-			return &fantasy.Response{
-				Content: []fantasy.Content{
-					fantasy.TextContent{Text: "summary"},
-				},
+			return func(yield func(fantasy.StreamPart) bool) {
+				yield(fantasy.StreamPart{Type: fantasy.StreamPartTypeTextStart, ID: "text"})
+				yield(fantasy.StreamPart{Type: fantasy.StreamPartTypeTextDelta, ID: "text", Delta: "summary"})
+				yield(fantasy.StreamPart{Type: fantasy.StreamPartTypeTextEnd, ID: "text"})
+				yield(fantasy.StreamPart{Type: fantasy.StreamPartTypeFinish, FinishReason: fantasy.FinishReasonStop})
 			}, nil
 		},
 	}
diff --git a/coderd/x/chatd/compaction_hooks_test.go b/coderd/x/chatd/compaction_hooks_test.go
index 60a1360386..667bc317ca 100644
--- a/coderd/x/chatd/compaction_hooks_test.go
+++ b/coderd/x/chatd/compaction_hooks_test.go
@@ -146,11 +146,11 @@ func TestManualCompactionPostCompactEffects(t *testing.T) {
 			var compactionCalls atomic.Int32
 			anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 				body := anthropicRequestBody(t, *req)
+				if strings.Contains(body, "You are performing a context compaction") {
+					compactionCalls.Add(1)
+					return anthropicCompactionResponse(t, req, "manual hook compaction summary")
+				}
 				if !req.Stream {
-					if strings.Contains(body, "You are performing a context compaction") {
-						compactionCalls.Add(1)
-						return anthropicCompactionResponse("manual hook compaction summary")
-					}
 					return chattest.AnthropicNonStreamingResponse("title")
 				}
 				// Low usage keeps automatic compaction out of the way, so
@@ -232,12 +232,16 @@ func startCompactionHookChat(
 	var streamCalls atomic.Int32
 	anthropicURL := chattest.NewAnthropic(t, func(req *chattest.AnthropicRequest) chattest.AnthropicResponse {
 		body := anthropicRequestBody(t, *req)
+		if strings.Contains(body, "You are performing a context compaction") {
+			compactionCalls.Add(1)
+			inspectCompaction(t, body)
+			// The 32000 default cap with 50% headroom. The remaining
+			// window (100 limit - 80 input - trigger output - summary
+			// prompt reserve) is non-positive, so the cap is unchanged.
+			require.Equal(t, 48000, req.MaxTokens)
+			return anthropicCompactionResponse(t, req, "hook compaction summary")
+		}
 		if !req.Stream {
-			if strings.Contains(body, "You are performing a context compaction") {
-				compactionCalls.Add(1)
-				inspectCompaction(t, body)
-				return anthropicCompactionResponse("hook compaction summary")
-			}
 			return chattest.AnthropicNonStreamingResponse("title")
 		}
 		if streamCalls.Add(1) == 1 {
diff --git a/coderd/x/chatd/generation_preparer_internal_test.go b/coderd/x/chatd/generation_preparer_internal_test.go
index 19fa19705a..1ee588d362 100644
--- a/coderd/x/chatd/generation_preparer_internal_test.go
+++ b/coderd/x/chatd/generation_preparer_internal_test.go
@@ -182,9 +182,8 @@ func TestPrepareGenerationClampsRequestedReasoningEffortToMax(t *testing.T) {
 	require.Equal(t, prepared.CallTemplate.ProviderOptions, summaryCall.ProviderOptions)
 	require.NotNil(t, summaryCall.ToolChoice)
 	require.Equal(t, fantasy.ToolChoiceNone, *summaryCall.ToolChoice)
-	// Non-streaming summaries must not inherit the default output cap the
-	// Anthropic SDK rejects.
-	require.Nil(t, summaryCall.MaxOutputTokens)
+	require.NotNil(t, summaryCall.MaxOutputTokens)
+	require.Equal(t, 3*defaultChatMaxOutputTokens/2, *summaryCall.MaxOutputTokens)
 }
 
 func TestPrepareGenerationReplacesUnsupportedToolMedia(t *testing.T) {
diff --git a/coderd/x/chatd/modelcall.go b/coderd/x/chatd/modelcall.go
index d4bff14127..af75512dfb 100644
--- a/coderd/x/chatd/modelcall.go
+++ b/coderd/x/chatd/modelcall.go
@@ -199,14 +199,22 @@ func (r resolvedModelCall) newCall() fantasy.Call {
 }
 
 // compactionSummaryCall follows the resolved call template, except summaries
-// must not call tools and must not carry the default output cap: the summary
-// request is non-streaming, and the Anthropic SDK rejects non-streaming
-// requests whose max_tokens implies a completion longer than ten minutes.
+// must not call tools. Streaming avoids the Anthropic SDK's non-streaming
+// duration limit, while the explicit cap prevents adaptive thinking from
+// exhausting fantasy's smaller provider default before producing summary text.
+// The cap gets 50% headroom because the summary must fit reasoning plus
+// summary text in one response; a low configured chat cap could otherwise
+// truncate the summary that replaces pruned history. The headroom stays
+// modest because a cap configured at a provider's output ceiling overshoots
+// it; that residual overshoot is an accepted tradeoff. GenerateCompaction
+// bounds the increased cap by the remaining context window at trigger time.
 func compactionSummaryCall(resolved resolvedModelCall) fantasy.Call {
 	call := resolved.newCall()
 	toolChoiceNone := fantasy.ToolChoiceNone
 	call.ToolChoice = &toolChoiceNone
-	call.MaxOutputTokens = nil
+	if call.MaxOutputTokens != nil {
+		call.MaxOutputTokens = ptr.Ref(*call.MaxOutputTokens * 3 / 2)
+	}
 	return call
 }