diff --git a/agent/agentproc/api.go b/agent/agentproc/api.go
index f784d0e898..bf974b6307 100644
--- a/agent/agentproc/api.go
+++ b/agent/agentproc/api.go
@@ -1,11 +1,13 @@
 package agentproc
 
 import (
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
 	"net/http"
 	"sort"
+	"time"
 
 	"github.com/go-chi/chi/v5"
 	"github.com/google/uuid"
@@ -18,6 +20,13 @@ import (
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 )
 
+const (
+	// maxWaitDuration is the maximum time a blocking
+	// process output request can wait, regardless of
+	// what the client requests.
+	maxWaitDuration = 5 * time.Minute
+)
+
 // API exposes process-related operations through the agent.
 type API struct {
 	logger    slog.Logger
@@ -163,6 +172,30 @@ func (api *API) handleProcessOutput(rw http.ResponseWriter, r *http.Request) {
 		}
 	}
 
+	// Check for blocking mode via query params.
+	waitStr := r.URL.Query().Get("wait")
+	wantWait := waitStr == "true"
+
+	if wantWait {
+		// Extend the write deadline so the HTTP server's
+		// WriteTimeout does not kill the connection while
+		// we block.
+		rc := http.NewResponseController(rw)
+		if err := rc.SetWriteDeadline(time.Now().Add(maxWaitDuration)); err != nil {
+			api.logger.Error(ctx, "extend write deadline for blocking process output",
+				slog.Error(err),
+			)
+		}
+
+		// Cap the wait at maxWaitDuration regardless of
+		// client-supplied timeout.
+		waitCtx, waitCancel := context.WithTimeout(ctx, maxWaitDuration)
+		defer waitCancel()
+
+		_ = proc.waitForOutput(waitCtx)
+		// Fall through to read snapshot below.
+	}
+
 	output, truncated := proc.output()
 	info := proc.info()
 
diff --git a/agent/agentproc/api_test.go b/agent/agentproc/api_test.go
index c7157c1730..eddbe2d6f9 100644
--- a/agent/agentproc/api_test.go
+++ b/agent/agentproc/api_test.go
@@ -10,6 +10,7 @@ import (
 	"os"
 	"runtime"
 	"strings"
+	"sync"
 	"testing"
 	"time"
 
@@ -783,6 +784,133 @@ func TestProcessOutput(t *testing.T) {
 		w2 := getOutput(t, handler, id)
 		require.Equal(t, http.StatusOK, w2.Code)
 	})
+
+	t.Run("WaitForExit", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo hello-wait && sleep 0.1",
+		})
+
+		w := getOutputWithWait(t, handler, id)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ProcessOutputResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.False(t, resp.Running)
+		require.NotNil(t, resp.ExitCode)
+		require.Equal(t, 0, *resp.ExitCode)
+		require.Contains(t, resp.Output, "hello-wait")
+	})
+
+	t.Run("WaitAlreadyExited", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command: "echo done",
+		})
+
+		waitForExit(t, handler, id)
+
+		w := getOutputWithWait(t, handler, id)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ProcessOutputResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.False(t, resp.Running)
+		require.Contains(t, resp.Output, "done")
+	})
+
+	t.Run("WaitTimeout", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command:    "sleep 300",
+			Background: true,
+		})
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.IntervalMedium)
+		defer cancel()
+
+		w := getOutputWithWaitCtx(ctx, t, handler, id)
+		require.Equal(t, http.StatusOK, w.Code)
+
+		var resp workspacesdk.ProcessOutputResponse
+		err := json.NewDecoder(w.Body).Decode(&resp)
+		require.NoError(t, err)
+		require.True(t, resp.Running)
+
+		// Kill and wait for the process so cleanup does
+		// not hang.
+		postSignal(
+			t, handler, id,
+			workspacesdk.SignalProcessRequest{Signal: "kill"},
+		)
+		waitForExit(t, handler, id)
+	})
+
+	t.Run("ConcurrentWaiters", func(t *testing.T) {
+		t.Parallel()
+
+		handler := newTestAPI(t)
+
+		id := startAndGetID(t, handler, workspacesdk.StartProcessRequest{
+			Command:    "sleep 300",
+			Background: true,
+		})
+
+		var (
+			wg    sync.WaitGroup
+			resps [2]workspacesdk.ProcessOutputResponse
+			codes [2]int
+		)
+		for i := range 2 {
+			wg.Add(1)
+			go func() {
+				defer wg.Done()
+				w := getOutputWithWait(t, handler, id)
+				codes[i] = w.Code
+				_ = json.NewDecoder(w.Body).Decode(&resps[i])
+			}()
+		}
+
+		// Signal the process to exit so both waiters unblock.
+		postSignal(
+			t, handler, id,
+			workspacesdk.SignalProcessRequest{Signal: "kill"},
+		)
+
+		wg.Wait()
+
+		for i := range 2 {
+			require.Equal(t, http.StatusOK, codes[i], "waiter %d", i)
+			require.False(t, resps[i].Running, "waiter %d", i)
+		}
+	})
+}
+
+func getOutputWithWait(t *testing.T, handler http.Handler, id string) *httptest.ResponseRecorder {
+	t.Helper()
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+	return getOutputWithWaitCtx(ctx, t, handler, id)
+}
+
+func getOutputWithWaitCtx(ctx context.Context, t *testing.T, handler http.Handler, id string) *httptest.ResponseRecorder {
+	t.Helper()
+	path := fmt.Sprintf("/%s/output?wait=true", id)
+	req := httptest.NewRequestWithContext(ctx, http.MethodGet, path, nil)
+	w := httptest.NewRecorder()
+	handler.ServeHTTP(w, req)
+	return w
 }
 
 func TestSignalProcess(t *testing.T) {
diff --git a/agent/agentproc/headtail.go b/agent/agentproc/headtail.go
index 34c07101ae..b1e65e369b 100644
--- a/agent/agentproc/headtail.go
+++ b/agent/agentproc/headtail.go
@@ -39,11 +39,13 @@ const (
 // how much output is written.
 type HeadTailBuffer struct {
 	mu         sync.Mutex
+	cond       *sync.Cond
 	head       []byte
 	tail       []byte
 	tailPos    int
 	tailFull   bool
 	headFull   bool
+	closed     bool
 	totalBytes int
 	maxHead    int
 	maxTail    int
@@ -52,20 +54,24 @@ type HeadTailBuffer struct {
 // NewHeadTailBuffer creates a new HeadTailBuffer with the
 // default head and tail sizes.
 func NewHeadTailBuffer() *HeadTailBuffer {
-	return &HeadTailBuffer{
+	b := &HeadTailBuffer{
 		maxHead: MaxHeadBytes,
 		maxTail: MaxTailBytes,
 	}
+	b.cond = sync.NewCond(&b.mu)
+	return b
 }
 
 // NewHeadTailBufferSized creates a HeadTailBuffer with custom
 // head and tail sizes. This is useful for testing truncation
 // logic with smaller buffers.
 func NewHeadTailBufferSized(maxHead, maxTail int) *HeadTailBuffer {
-	return &HeadTailBuffer{
+	b := &HeadTailBuffer{
 		maxHead: maxHead,
 		maxTail: maxTail,
 	}
+	b.cond = sync.NewCond(&b.mu)
+	return b
 }
 
 // Write implements io.Writer. It is safe for concurrent use.
@@ -296,6 +302,15 @@ func truncateLines(s string) string {
 	return b.String()
 }
 
+// Close marks the buffer as closed and wakes any waiters.
+// This is called when the process exits.
+func (b *HeadTailBuffer) Close() {
+	b.mu.Lock()
+	defer b.mu.Unlock()
+	b.closed = true
+	b.cond.Broadcast()
+}
+
 // Reset clears the buffer, discarding all data.
 func (b *HeadTailBuffer) Reset() {
 	b.mu.Lock()
@@ -305,5 +320,7 @@ func (b *HeadTailBuffer) Reset() {
 	b.tailPos = 0
 	b.tailFull = false
 	b.headFull = false
+	b.closed = false
 	b.totalBytes = 0
+	b.cond.Broadcast()
 }
diff --git a/agent/agentproc/process.go b/agent/agentproc/process.go
index ed1279409c..3a457387dc 100644
--- a/agent/agentproc/process.go
+++ b/agent/agentproc/process.go
@@ -208,6 +208,9 @@ func (m *manager) start(req workspacesdk.StartProcessRequest, chatID string) (*p
 		proc.exitCode = &code
 		proc.mu.Unlock()
 
+		// Wake any waiters blocked on new output or
+		// process exit before closing the done channel.
+		proc.buf.Close()
 		close(proc.done)
 	}()
 
@@ -320,6 +323,36 @@ func (m *manager) Close() error {
 	return nil
 }
 
+// waitForOutput blocks until the buffer is closed (process
+// exited) or the context is canceled. Returns nil when the
+// buffer closed, ctx.Err() when the context expired.
+func (p *process) waitForOutput(ctx context.Context) error {
+	p.buf.cond.L.Lock()
+	defer p.buf.cond.L.Unlock()
+
+	nevermind := make(chan struct{})
+	defer close(nevermind)
+	go func() {
+		select {
+		case <-ctx.Done():
+			// Acquire the lock before broadcasting to
+			// guarantee the waiter has entered cond.Wait()
+			// (which atomically releases the lock).
+			// Without this, a Broadcast between the loop
+			// predicate check and cond.Wait() is lost.
+			p.buf.cond.L.Lock()
+			defer p.buf.cond.L.Unlock()
+			p.buf.cond.Broadcast()
+		case <-nevermind:
+		}
+	}()
+
+	for ctx.Err() == nil && !p.buf.closed {
+		p.buf.cond.Wait()
+	}
+	return ctx.Err()
+}
+
 // resolveWorkDir returns the directory a process should start in.
 // Priority: explicit request dir > agent configured dir > $HOME.
 // Falls through when a candidate is empty or does not exist on
diff --git a/coderd/chatd/chatd_test.go b/coderd/chatd/chatd_test.go
index 02f6b4b408..9fd13005fb 100644
--- a/coderd/chatd/chatd_test.go
+++ b/coderd/chatd/chatd_test.go
@@ -1590,7 +1590,7 @@ func TestPersistToolResultWithBinaryData(t *testing.T) {
 		}).
 		Times(1)
 	mockConn.EXPECT().
-		ProcessOutput(gomock.Any(), "proc-binary").
+		ProcessOutput(gomock.Any(), "proc-binary", gomock.Any()).
 		Return(workspacesdk.ProcessOutputResponse{
 			Output:   string(binaryOutput),
 			Running:  false,
diff --git a/coderd/chatd/chattool/execute.go b/coderd/chatd/chattool/execute.go
index d7b2203ff4..4b64df1e89 100644
--- a/coderd/chatd/chattool/execute.go
+++ b/coderd/chatd/chattool/execute.go
@@ -3,14 +3,12 @@ package chattool
 import (
 	"context"
 	"encoding/json"
-	"errors"
 	"fmt"
 	"regexp"
 	"strings"
 	"time"
 
 	"charm.land/fantasy"
-	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 )
@@ -23,9 +21,10 @@ const (
 	// maxOutputToModel is the maximum output sent to the LLM.
 	maxOutputToModel = 32 << 10 // 32KB
 
-	// pollInterval is how often we check for process completion
-	// in foreground mode.
-	pollInterval = 200 * time.Millisecond
+	// snapshotTimeout is how long a non-blocking fallback
+	// request is allowed to take when retrieving a process
+	// output snapshot after a blocking wait times out.
+	snapshotTimeout = 30 * time.Second
 )
 
 // nonInteractiveEnvVars are set on every process to prevent
@@ -89,7 +88,7 @@ type ExecuteArgs struct {
 func Execute(options ExecuteOptions) fantasy.AgentTool {
 	return fantasy.NewAgentTool(
 		"execute",
-		"Execute a shell command in the workspace. Use run_in_background=true for long-running processes (dev servers, file watchers, builds). Never use shell '&' for backgrounding.",
+		"Execute a shell command in the workspace. Use run_in_background=true for long-running processes (dev servers, file watchers, builds). Never use shell '&' for backgrounding. If the command times out, the response includes a background_process_id so you can retrieve output later with process_output.",
 		func(ctx context.Context, args ExecuteArgs, _ fantasy.ToolCall) (fantasy.ToolResponse, error) {
 			if options.GetWorkspaceConn == nil {
 				return fantasy.NewTextErrorResponse("workspace connection resolver is not configured"), nil
@@ -173,7 +172,7 @@ func executeBackground(
 	return fantasy.NewTextResponse(string(data))
 }
 
-// executeForeground starts a process and polls for its
+// executeForeground starts a process and waits for its
 // completion, enforcing the configured timeout.
 func executeForeground(
 	ctx context.Context,
@@ -212,7 +211,7 @@ func executeForeground(
 		return errorResult(fmt.Sprintf("start process: %v", err))
 	}
 
-	result := pollProcess(cmdCtx, conn, resp.ID, timeout)
+	result := waitForProcess(cmdCtx, conn, resp.ID, timeout)
 	result.WallDurationMs = time.Since(start).Milliseconds()
 
 	// Add an advisory note for file-dump commands.
@@ -237,62 +236,84 @@ func truncateOutput(output string) string {
 	return output
 }
 
-// pollProcess polls for process output until the process exits
-// or the context times out.
-func pollProcess(
+// waitForProcess waits for process completion using the
+// blocking process output API instead of polling.
+func waitForProcess(
 	ctx context.Context,
 	conn workspacesdk.AgentConn,
 	processID string,
 	timeout time.Duration,
 ) ExecuteResult {
-	ticker := time.NewTicker(pollInterval)
-	defer ticker.Stop()
-
-	for {
-		select {
-		case <-ctx.Done():
-			// Timeout — get whatever output we have. Use a
-			// fresh context since cmdCtx is already canceled.
+	// Block until the process exits or the context is
+	// canceled.
+	resp, err := conn.ProcessOutput(ctx, processID, &workspacesdk.ProcessOutputOptions{
+		Wait: true,
+	})
+	if err != nil {
+		if ctx.Err() != nil {
+			// Timeout: fetch final snapshot with a fresh
+			// context. The blocking request was canceled
+			// so the response body was lost.
 			bgCtx, bgCancel := context.WithTimeout(
 				context.Background(),
-				5*time.Second,
+				snapshotTimeout,
 			)
-			outputResp, outputErr := conn.ProcessOutput(bgCtx, processID)
-			bgCancel()
-			output := truncateOutput(outputResp.Output)
-			timeoutErr := xerrors.Errorf("command timed out after %s", timeout)
-			if outputErr != nil {
-				timeoutErr = errors.Join(timeoutErr, xerrors.Errorf("failed to get output: %w", outputErr))
-			}
-			return ExecuteResult{
-				Success:   false,
-				Output:    output,
-				ExitCode:  -1,
-				Error:     timeoutErr.Error(),
-				Truncated: outputResp.Truncated,
-			}
-		case <-ticker.C:
-			outputResp, err := conn.ProcessOutput(ctx, processID)
+			defer bgCancel()
+			resp, err = conn.ProcessOutput(bgCtx, processID, nil)
 			if err != nil {
 				return ExecuteResult{
-					Success: false,
-					Error:   fmt.Sprintf("get process output: %v", err),
+					Success:             false,
+					ExitCode:            -1,
+					Error:               fmt.Sprintf("command timed out after %s; failed to get output: %v", timeout, err),
+					BackgroundProcessID: processID,
 				}
 			}
-			if !outputResp.Running {
-				exitCode := 0
-				if outputResp.ExitCode != nil {
-					exitCode = *outputResp.ExitCode
-				}
-				output := truncateOutput(outputResp.Output)
-				return ExecuteResult{
-					Success:   exitCode == 0,
-					Output:    output,
-					ExitCode:  exitCode,
-					Truncated: outputResp.Truncated,
-				}
+			output := truncateOutput(resp.Output)
+			return ExecuteResult{
+				Success:             false,
+				Output:              output,
+				ExitCode:            -1,
+				Error:               fmt.Sprintf("command timed out after %s", timeout),
+				Truncated:           resp.Truncated,
+				BackgroundProcessID: processID,
 			}
 		}
+		return ExecuteResult{
+			Success: false,
+			Error:   fmt.Sprintf("get process output: %v", err),
+		}
+	}
+
+	// The server-side wait may return before the
+	// process exits if maxWaitDuration is shorter than
+	// the client's timeout. Retry if our context still
+	// has time left.
+	if resp.Running {
+		if ctx.Err() == nil {
+			// Still within the caller's timeout, retry.
+			return waitForProcess(ctx, conn, processID, timeout)
+		}
+		output := truncateOutput(resp.Output)
+		return ExecuteResult{
+			Success:             false,
+			Output:              output,
+			ExitCode:            -1,
+			Error:               fmt.Sprintf("command timed out after %s", timeout),
+			Truncated:           resp.Truncated,
+			BackgroundProcessID: processID,
+		}
+	}
+
+	exitCode := 0
+	if resp.ExitCode != nil {
+		exitCode = *resp.ExitCode
+	}
+	output := truncateOutput(resp.Output)
+	return ExecuteResult{
+		Success:   exitCode == 0,
+		Output:    output,
+		ExitCode:  exitCode,
+		Truncated: resp.Truncated,
 	}
 }
 
@@ -322,10 +343,19 @@ func detectFileDump(command string) string {
 	return ""
 }
 
+const (
+	// defaultProcessOutputTimeout is the default time the
+	// process_output tool blocks waiting for new output or
+	// process exit before returning. This avoids polling
+	// loops that waste tokens and HTTP round-trips.
+	defaultProcessOutputTimeout = 10 * time.Second
+)
+
 // ProcessOutputArgs are the parameters accepted by the
 // process_output tool.
 type ProcessOutputArgs struct {
-	ProcessID string `json:"process_id"`
+	ProcessID   string  `json:"process_id"`
+	WaitTimeout *string `json:"wait_timeout,omitempty" description:"Override the default 10s block duration. The call blocks until the process exits or this timeout is reached. Set to '0s' for an immediate snapshot without waiting."`
 }
 
 // ProcessOutput returns an AgentTool that retrieves the output
@@ -335,9 +365,13 @@ func ProcessOutput(options ProcessToolOptions) fantasy.AgentTool {
 		"process_output",
 		"Retrieve output from a background process. "+
 			"Use the process_id returned by execute with "+
-			"run_in_background=true. Returns the current output, "+
-			"whether the process is still running, and the exit "+
-			"code if it has finished.",
+			"run_in_background=true or from a timed-out "+
+			"execute's background_process_id. Blocks up to "+
+			"10s for the process to exit, then returns the "+
+			"output and exit_code. If still running after "+
+			"the timeout, returns the output so far. Use "+
+			"wait_timeout to override the default 10s wait "+
+			"(e.g. '30s', or '0s' for an immediate snapshot).",
 		func(ctx context.Context, args ProcessOutputArgs, _ fantasy.ToolCall) (fantasy.ToolResponse, error) {
 			if options.GetWorkspaceConn == nil {
 				return fantasy.NewTextErrorResponse("workspace connection resolver is not configured"), nil
@@ -349,9 +383,42 @@ func ProcessOutput(options ProcessToolOptions) fantasy.AgentTool {
 			if err != nil {
 				return fantasy.NewTextErrorResponse(err.Error()), nil
 			}
-			resp, err := conn.ProcessOutput(ctx, args.ProcessID)
+
+			timeout := defaultProcessOutputTimeout
+			if args.WaitTimeout != nil {
+				parsed, err := time.ParseDuration(*args.WaitTimeout)
+				if err != nil {
+					return fantasy.NewTextErrorResponse(
+						fmt.Sprintf("invalid wait_timeout %q: %v", *args.WaitTimeout, err),
+					), nil
+				}
+				timeout = parsed
+			}
+			var opts *workspacesdk.ProcessOutputOptions
+			// Save parent context before applying timeout.
+			parentCtx := ctx
+			if timeout > 0 {
+				opts = &workspacesdk.ProcessOutputOptions{
+					Wait: true,
+				}
+				var cancel context.CancelFunc
+				ctx, cancel = context.WithTimeout(ctx, timeout)
+				defer cancel()
+			}
+			resp, err := conn.ProcessOutput(ctx, args.ProcessID, opts)
 			if err != nil {
-				return errorResult(fmt.Sprintf("get process output: %v", err)), nil
+				// If our wait timed out but the parent is still alive,
+				// fetch a non-blocking snapshot.
+				if ctx.Err() == nil || parentCtx.Err() != nil {
+					return errorResult(fmt.Sprintf("get process output: %v", err)), nil
+				}
+				bgCtx, bgCancel := context.WithTimeout(parentCtx, snapshotTimeout)
+				defer bgCancel()
+				resp, err = conn.ProcessOutput(bgCtx, args.ProcessID, nil)
+				if err != nil {
+					return errorResult(fmt.Sprintf("get process output: %v", err)), nil
+				}
+				// Fall through to normal response handling below.
 			}
 			output := truncateOutput(resp.Output)
 			exitCode := 0
@@ -365,7 +432,7 @@ func ProcessOutput(options ProcessToolOptions) fantasy.AgentTool {
 				Truncated: resp.Truncated,
 			}
 			if resp.Running {
-				// Process is still running — success is not
+				// Process is still running, success is not
 				// yet determined.
 				result.Success = true
 				result.Note = "process is still running"
diff --git a/coderd/chatd/chattool/execute_internal_test.go b/coderd/chatd/chattool/execute_internal_test.go
index e9100f3051..dd3ee84940 100644
--- a/coderd/chatd/chattool/execute_internal_test.go
+++ b/coderd/chatd/chattool/execute_internal_test.go
@@ -74,7 +74,7 @@ func runForegroundWithOutput(t *testing.T, output string) ExecuteResult {
 		Return(workspacesdk.StartProcessResponse{ID: "proc-1"}, nil)
 	exitCode := 0
 	mockConn.EXPECT().
-		ProcessOutput(gomock.Any(), "proc-1").
+		ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 		Return(workspacesdk.ProcessOutputResponse{
 			Running:  false,
 			ExitCode: &exitCode,
diff --git a/coderd/chatd/chattool/execute_test.go b/coderd/chatd/chattool/execute_test.go
index c89086c219..3d22cee96f 100644
--- a/coderd/chatd/chattool/execute_test.go
+++ b/coderd/chatd/chattool/execute_test.go
@@ -121,7 +121,7 @@ func TestExecuteTool(t *testing.T) {
 				// For foreground cases, ProcessOutput is polled.
 				exitCode := 0
 				mockConn.EXPECT().
-					ProcessOutput(gomock.Any(), "proc-1").
+					ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 					Return(workspacesdk.ProcessOutputResponse{
 						Running:  false,
 						ExitCode: &exitCode,
@@ -177,7 +177,7 @@ func TestExecuteTool(t *testing.T) {
 			})
 		exitCode := 0
 		mockConn.EXPECT().
-			ProcessOutput(gomock.Any(), "proc-1").
+			ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 			Return(workspacesdk.ProcessOutputResponse{
 				Running:  false,
 				ExitCode: &exitCode,
@@ -213,7 +213,7 @@ func TestExecuteTool(t *testing.T) {
 			Return(workspacesdk.StartProcessResponse{ID: "proc-1"}, nil)
 		exitCode := 42
 		mockConn.EXPECT().
-			ProcessOutput(gomock.Any(), "proc-1").
+			ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 			Return(workspacesdk.ProcessOutputResponse{
 				Running:  false,
 				ExitCode: &exitCode,
@@ -274,23 +274,27 @@ func TestExecuteTool(t *testing.T) {
 			StartProcess(gomock.Any(), gomock.Any()).
 			Return(workspacesdk.StartProcessResponse{ID: "proc-1"}, nil)
 
-		// ProcessOutput always returns running. The poll loop
-		// and the timeout-branch recovery call both hit this.
+		// First call (blocking wait) returns context error
+		// because the 50ms timeout expires.
 		mockConn.EXPECT().
-			ProcessOutput(gomock.Any(), "proc-1").
+			ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
+			DoAndReturn(func(ctx context.Context, _ string, _ *workspacesdk.ProcessOutputOptions) (workspacesdk.ProcessOutputResponse, error) {
+				<-ctx.Done()
+				return workspacesdk.ProcessOutputResponse{}, ctx.Err()
+			})
+		// Second call (snapshot fallback) returns partial output.
+		mockConn.EXPECT().
+			ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 			Return(workspacesdk.ProcessOutputResponse{
 				Running: true,
 				Output:  "partial output",
-			}, nil).
-			AnyTimes()
-
+			}, nil)
 		tool := newExecuteTool(t, mockConn)
 		ctx := testutil.Context(t, testutil.WaitMedium)
 		resp, err := tool.Run(ctx, fantasy.ToolCall{
 			ID:   "call-1",
 			Name: "execute",
-			// 50ms timeout expires before the 200ms poll interval,
-			// so the context-done branch fires first.
+			// 50ms timeout expires during the blocking wait.
 			Input: `{"command":"sleep 999","timeout":"50ms"}`,
 		})
 		require.NoError(t, err)
@@ -340,7 +344,7 @@ func TestExecuteTool(t *testing.T) {
 			StartProcess(gomock.Any(), gomock.Any()).
 			Return(workspacesdk.StartProcessResponse{ID: "proc-1"}, nil)
 		mockConn.EXPECT().
-			ProcessOutput(gomock.Any(), "proc-1").
+			ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 			Return(workspacesdk.ProcessOutputResponse{}, xerrors.New("agent disconnected"))
 
 		tool := newExecuteTool(t, mockConn)
@@ -440,7 +444,7 @@ func TestDetectFileDump(t *testing.T) {
 				Return(workspacesdk.StartProcessResponse{ID: "proc-1"}, nil)
 			exitCode := 0
 			mockConn.EXPECT().
-				ProcessOutput(gomock.Any(), "proc-1").
+				ProcessOutput(gomock.Any(), "proc-1", gomock.Any()).
 				Return(workspacesdk.ProcessOutputResponse{
 					Running:  false,
 					ExitCode: &exitCode,
diff --git a/codersdk/workspacesdk/agentconn.go b/codersdk/workspacesdk/agentconn.go
index c12d528b12..1cf8ca7a99 100644
--- a/codersdk/workspacesdk/agentconn.go
+++ b/codersdk/workspacesdk/agentconn.go
@@ -70,7 +70,7 @@ type AgentConn interface {
 	ListeningPorts(ctx context.Context) (codersdk.WorkspaceAgentListeningPortsResponse, error)
 	Netcheck(ctx context.Context) (healthsdk.AgentNetcheckReport, error)
 	Ping(ctx context.Context) (time.Duration, bool, *ipnstate.PingResult, error)
-	ProcessOutput(ctx context.Context, id string) (ProcessOutputResponse, error)
+	ProcessOutput(ctx context.Context, id string, opts *ProcessOutputOptions) (ProcessOutputResponse, error)
 	PrometheusMetrics(ctx context.Context) ([]byte, error)
 	ReconnectingPTY(ctx context.Context, id uuid.UUID, height uint16, width uint16, command string, initOpts ...AgentReconnectingPTYInitOption) (net.Conn, error)
 	DeleteDevcontainer(ctx context.Context, devcontainerID string) error
@@ -715,6 +715,14 @@ type ProcessOutputResponse struct {
 	ExitCode  *int               `json:"exit_code,omitempty"`
 }
 
+// ProcessOutputOptions configures blocking behavior for
+// process output retrieval.
+type ProcessOutputOptions struct {
+	// Wait enables blocking mode. When true, the request
+	// blocks until the process exits or the context expires.
+	Wait bool
+}
+
 // ProcessTruncation describes how process output was truncated.
 type ProcessTruncation struct {
 	OriginalBytes int    `json:"original_bytes"`
@@ -946,10 +954,14 @@ func (c *agentConn) ListProcesses(ctx context.Context) (ListProcessesResponse, e
 }
 
 // ProcessOutput returns the output of a tracked process on the agent.
-func (c *agentConn) ProcessOutput(ctx context.Context, id string) (ProcessOutputResponse, error) {
+func (c *agentConn) ProcessOutput(ctx context.Context, id string, opts *ProcessOutputOptions) (ProcessOutputResponse, error) {
 	ctx, span := tracing.StartSpan(ctx)
 	defer span.End()
-	res, err := c.apiRequest(ctx, http.MethodGet, "/api/v0/processes/"+id+"/output", nil)
+	path := "/api/v0/processes/" + id + "/output"
+	if opts != nil && opts.Wait {
+		path += "?wait=true"
+	}
+	res, err := c.apiRequest(ctx, http.MethodGet, path, nil)
 	if err != nil {
 		return ProcessOutputResponse{}, xerrors.Errorf("do request: %w", err)
 	}
diff --git a/codersdk/workspacesdk/agentconnmock/agentconnmock.go b/codersdk/workspacesdk/agentconnmock/agentconnmock.go
index 3204e5947d..6a83a8bd8d 100644
--- a/codersdk/workspacesdk/agentconnmock/agentconnmock.go
+++ b/codersdk/workspacesdk/agentconnmock/agentconnmock.go
@@ -308,18 +308,18 @@ func (mr *MockAgentConnMockRecorder) Ping(ctx any) *gomock.Call {
 }
 
 // ProcessOutput mocks base method.
-func (m *MockAgentConn) ProcessOutput(ctx context.Context, id string) (workspacesdk.ProcessOutputResponse, error) {
+func (m *MockAgentConn) ProcessOutput(ctx context.Context, id string, opts *workspacesdk.ProcessOutputOptions) (workspacesdk.ProcessOutputResponse, error) {
 	m.ctrl.T.Helper()
-	ret := m.ctrl.Call(m, "ProcessOutput", ctx, id)
+	ret := m.ctrl.Call(m, "ProcessOutput", ctx, id, opts)
 	ret0, _ := ret[0].(workspacesdk.ProcessOutputResponse)
 	ret1, _ := ret[1].(error)
 	return ret0, ret1
 }
 
 // ProcessOutput indicates an expected call of ProcessOutput.
-func (mr *MockAgentConnMockRecorder) ProcessOutput(ctx, id any) *gomock.Call {
+func (mr *MockAgentConnMockRecorder) ProcessOutput(ctx, id, opts any) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ProcessOutput", reflect.TypeOf((*MockAgentConn)(nil).ProcessOutput), ctx, id)
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "ProcessOutput", reflect.TypeOf((*MockAgentConn)(nil).ProcessOutput), ctx, id, opts)
 }
 
 // PrometheusMetrics mocks base method.