diff --git a/claudetool/bash.go b/claudetool/bash.go
index a62892f..59b8e3c 100644
--- a/claudetool/bash.go
+++ b/claudetool/bash.go
@@ -23,44 +23,77 @@
 // PermissionCallback is a function type for checking if a command is allowed to run
 type PermissionCallback func(command string) error
 
-// BashTool is a struct for executing shell commands with bash -c and optional timeout
+// BashTool specifies a llm.Tool for executing shell commands.
 type BashTool struct {
 	// CheckPermission is called before running any command, if set
 	CheckPermission PermissionCallback
 	// EnableJITInstall enables just-in-time tool installation for missing commands
 	EnableJITInstall bool
+	// Timeouts holds the configurable timeout values (uses defaults if nil)
+	Timeouts *Timeouts
 }
 
 const (
 	EnableBashToolJITInstall = true
 	NoBashToolJITInstall     = false
+
+	DefaultFastTimeout       = 30 * time.Second
+	DefaultSlowTimeout       = 15 * time.Minute
+	DefaultBackgroundTimeout = 24 * time.Hour
 )
 
-// NewBashTool creates a new Bash tool with optional permission callback
-func NewBashTool(checkPermission PermissionCallback, enableJITInstall bool) *llm.Tool {
-	tool := &BashTool{
-		CheckPermission:  checkPermission,
-		EnableJITInstall: enableJITInstall,
-	}
+// Timeouts holds the configurable timeout values for bash commands.
+type Timeouts struct {
+	Fast       time.Duration // regular commands (e.g., ls, echo, simple scripts)
+	Slow       time.Duration // commands that may reasonably take longer (e.g., downloads, builds, tests)
+	Background time.Duration // background commands (e.g., servers, long-running processes)
+}
 
+// Fast returns t's fast timeout, or DefaultFastTimeout if t is nil.
+func (t *Timeouts) fast() time.Duration {
+	if t == nil {
+		return DefaultFastTimeout
+	}
+	return t.Fast
+}
+
+// Slow returns t's slow timeout, or DefaultSlowTimeout if t is nil.
+func (t *Timeouts) slow() time.Duration {
+	if t == nil {
+		return DefaultSlowTimeout
+	}
+	return t.Slow
+}
+
+// Background returns t's background timeout, or DefaultBackgroundTimeout if t is nil.
+func (t *Timeouts) background() time.Duration {
+	if t == nil {
+		return DefaultBackgroundTimeout
+	}
+	return t.Background
+}
+
+// Tool returns an llm.Tool based on b.
+func (b *BashTool) Tool() *llm.Tool {
 	return &llm.Tool{
 		Name:        bashName,
 		Description: strings.TrimSpace(bashDescription),
 		InputSchema: llm.MustSchema(bashInputSchema),
-		Run:         tool.Run,
+		Run:         b.Run,
 	}
 }
 
-// The Bash tool executes shell commands with bash -c and optional timeout
-var Bash = NewBashTool(nil, NoBashToolJITInstall)
-
 const (
 	bashName        = "bash"
 	bashDescription = `
-Executes a shell command using bash -c with an optional timeout, returning combined stdout and stderr.
-When run with background flag, the process may keep running after the tool call returns, and
-the agent can inspect the output by reading the output files. Use the background task when, for example,
-starting a server to test something. Be sure to kill the process group when done.
+Executes shell commands via bash -c, returning combined stdout/stderr.
+
+With background=true, returns immediately while process continues running
+with output redirected to files. Kill process group when done.
+Use background for servers/demos that need to stay running.
+
+MUST set slow_ok=true for potentially slow commands: builds, downloads,
+installs, tests, or any other substantive operation.
 `
 	// If you modify this, update the termui template for prettier rendering.
 	bashInputSchema = `
@@ -70,15 +103,15 @@
   "properties": {
     "command": {
       "type": "string",
-      "description": "Shell script to execute"
+      "description": "Shell to execute"
     },
-    "timeout": {
-      "type": "string",
-      "description": "Timeout as a Go duration string, defaults to 10s if background is false; 10m if background is true"
+    "slow_ok": {
+      "type": "boolean",
+      "description": "Use extended timeout"
     },
     "background": {
       "type": "boolean",
-      "description": "If true, executes the command in the background without waiting for completion"
+      "description": "Execute in background"
     }
   }
 }
@@ -87,7 +120,7 @@
 
 type bashInput struct {
 	Command    string `json:"command"`
-	Timeout    string `json:"timeout,omitempty"`
+	SlowOK     bool   `json:"slow_ok,omitempty"`
 	Background bool   `json:"background,omitempty"`
 }
 
@@ -97,19 +130,14 @@
 	StderrFile string `json:"stderr_file"`
 }
 
-func (i *bashInput) timeout() time.Duration {
-	if i.Timeout != "" {
-		dur, err := time.ParseDuration(i.Timeout)
-		if err == nil {
-			return dur
-		}
-	}
-
-	// Otherwise, use different defaults based on background mode
-	if i.Background {
-		return 10 * time.Minute
-	} else {
-		return 10 * time.Second
+func (i *bashInput) timeout(t *Timeouts) time.Duration {
+	switch {
+	case i.Background:
+		return t.background()
+	case i.SlowOK:
+		return t.slow()
+	default:
+		return t.fast()
 	}
 }
 
@@ -140,9 +168,11 @@
 		}
 	}
 
+	timeout := req.timeout(b.Timeouts)
+
 	// If Background is set to true, use executeBackgroundBash
 	if req.Background {
-		result, err := executeBackgroundBash(ctx, req)
+		result, err := executeBackgroundBash(ctx, req, timeout)
 		if err != nil {
 			return nil, err
 		}
@@ -156,7 +186,7 @@
 	}
 
 	// For foreground commands, use executeBash
-	out, execErr := executeBash(ctx, req)
+	out, execErr := executeBash(ctx, req, timeout)
 	if execErr != nil {
 		return nil, execErr
 	}
@@ -165,8 +195,8 @@
 
 const maxBashOutputLength = 131072
 
-func executeBash(ctx context.Context, req bashInput) (string, error) {
-	execCtx, cancel := context.WithTimeout(ctx, req.timeout())
+func executeBash(ctx context.Context, req bashInput, timeout time.Duration) (string, error) {
+	execCtx, cancel := context.WithTimeout(ctx, timeout)
 	defer cancel()
 
 	// Can't do the simple thing and call CombinedOutput because of the need to kill the process group.
@@ -218,7 +248,7 @@
 		if len(partialOutput) > maxBashOutputLength {
 			partialOutput = partialOutput[:maxBashOutputLength] + "\n[output truncated due to size]\n"
 		}
-		return "", fmt.Errorf("command timed out after %s\nCommand output (until it timed out):\n%s", req.timeout(), outstr)
+		return "", fmt.Errorf("command timed out after %s\nCommand output (until it timed out):\n%s", timeout, outstr)
 	}
 	if err != nil {
 		return "", fmt.Errorf("command failed: %w\n%s", err, outstr)
@@ -246,7 +276,7 @@
 }
 
 // executeBackgroundBash executes a command in the background and returns the pid and output file locations
-func executeBackgroundBash(ctx context.Context, req bashInput) (*BackgroundResult, error) {
+func executeBackgroundBash(ctx context.Context, req bashInput, timeout time.Duration) (*BackgroundResult, error) {
 	// Create temporary directory for output files
 	tmpDir, err := os.MkdirTemp("", "sketch-bg-")
 	if err != nil {
@@ -296,7 +326,6 @@
 
 	// Set up timeout handling if a timeout was specified
 	pid := cmd.Process.Pid
-	timeout := req.timeout()
 	if timeout > 0 {
 		// Launch a goroutine that will kill the process after the timeout
 		go func() {
@@ -377,7 +406,7 @@
 	}
 	subConvo := info.Convo.SubConvo()
 	subConvo.Hidden = true
-	subBash := NewBashTool(nil, NoBashToolJITInstall)
+	subBash := &BashTool{EnableJITInstall: NoBashToolJITInstall}
 
 	done := false
 	doneTool := &llm.Tool{
@@ -428,7 +457,7 @@
 	}
 
 	subConvo.Tools = []*llm.Tool{
-		subBash,
+		subBash.Tool(),
 		doneTool,
 	}
 
diff --git a/claudetool/bash_test.go b/claudetool/bash_test.go
index 6904447..98410d5 100644
--- a/claudetool/bash_test.go
+++ b/claudetool/bash_test.go
@@ -11,12 +11,60 @@
 	"time"
 )
 
+func TestBashSlowOk(t *testing.T) {
+	// Test that slow_ok flag is properly handled
+	t.Run("SlowOk Flag", func(t *testing.T) {
+		input := json.RawMessage(`{"command":"echo 'slow test'","slow_ok":true}`)
+
+		bashTool := (&BashTool{}).Tool()
+		result, err := bashTool.Run(context.Background(), input)
+		if err != nil {
+			t.Fatalf("Unexpected error: %v", err)
+		}
+
+		expected := "slow test\n"
+		if len(result) == 0 || result[0].Text != expected {
+			t.Errorf("Expected %q, got %q", expected, result[0].Text)
+		}
+	})
+
+	// Test that slow_ok with background works
+	t.Run("SlowOk with Background", func(t *testing.T) {
+		input := json.RawMessage(`{"command":"echo 'slow background test'","slow_ok":true,"background":true}`)
+
+		bashTool := (&BashTool{}).Tool()
+		result, err := bashTool.Run(context.Background(), input)
+		if err != nil {
+			t.Fatalf("Unexpected error: %v", err)
+		}
+
+		// Should return background result JSON
+		var bgResult BackgroundResult
+		resultStr := result[0].Text
+		if err := json.Unmarshal([]byte(resultStr), &bgResult); err != nil {
+			t.Fatalf("Failed to unmarshal background result: %v", err)
+		}
+
+		if bgResult.PID <= 0 {
+			t.Errorf("Invalid PID returned: %d", bgResult.PID)
+		}
+
+		// Clean up
+		os.Remove(bgResult.StdoutFile)
+		os.Remove(bgResult.StderrFile)
+		os.Remove(filepath.Dir(bgResult.StdoutFile))
+	})
+}
+
 func TestBashTool(t *testing.T) {
+	var bashTool BashTool
+	tool := bashTool.Tool()
+
 	// Test basic functionality
 	t.Run("Basic Command", func(t *testing.T) {
 		input := json.RawMessage(`{"command":"echo 'Hello, world!'"}`)
 
-		result, err := Bash.Run(context.Background(), input)
+		result, err := tool.Run(context.Background(), input)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -31,7 +79,7 @@
 	t.Run("Command With Arguments", func(t *testing.T) {
 		input := json.RawMessage(`{"command":"echo -n foo && echo -n bar"}`)
 
-		result, err := Bash.Run(context.Background(), input)
+		result, err := tool.Run(context.Background(), input)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -42,21 +90,21 @@
 		}
 	})
 
-	// Test with timeout parameter
-	t.Run("With Timeout", func(t *testing.T) {
+	// Test with slow_ok parameter
+	t.Run("With SlowOK", func(t *testing.T) {
 		inputObj := struct {
 			Command string `json:"command"`
-			Timeout string `json:"timeout"`
+			SlowOK  bool   `json:"slow_ok"`
 		}{
 			Command: "sleep 0.1 && echo 'Completed'",
-			Timeout: "5s",
+			SlowOK:  true,
 		}
 		inputJSON, err := json.Marshal(inputObj)
 		if err != nil {
 			t.Fatalf("Failed to marshal input: %v", err)
 		}
 
-		result, err := Bash.Run(context.Background(), inputJSON)
+		result, err := tool.Run(context.Background(), inputJSON)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -67,21 +115,22 @@
 		}
 	})
 
-	// Test command timeout
+	// Test command timeout with custom timeout config
 	t.Run("Command Timeout", func(t *testing.T) {
-		inputObj := struct {
-			Command string `json:"command"`
-			Timeout string `json:"timeout"`
-		}{
-			Command: "sleep 0.5 && echo 'Should not see this'",
-			Timeout: "100ms",
+		// Use a custom BashTool with very short timeout
+		customTimeouts := &Timeouts{
+			Fast:       100 * time.Millisecond,
+			Slow:       100 * time.Millisecond,
+			Background: 100 * time.Millisecond,
 		}
-		inputJSON, err := json.Marshal(inputObj)
-		if err != nil {
-			t.Fatalf("Failed to marshal input: %v", err)
+		customBash := &BashTool{
+			Timeouts: customTimeouts,
 		}
+		tool := customBash.Tool()
 
-		_, err = Bash.Run(context.Background(), inputJSON)
+		input := json.RawMessage(`{"command":"sleep 0.5 && echo 'Should not see this'"}`)
+
+		_, err := tool.Run(context.Background(), input)
 		if err == nil {
 			t.Errorf("Expected timeout error, got none")
 		} else if !strings.Contains(err.Error(), "timed out") {
@@ -93,7 +142,7 @@
 	t.Run("Failed Command", func(t *testing.T) {
 		input := json.RawMessage(`{"command":"exit 1"}`)
 
-		_, err := Bash.Run(context.Background(), input)
+		_, err := tool.Run(context.Background(), input)
 		if err == nil {
 			t.Errorf("Expected error for failed command, got none")
 		}
@@ -103,7 +152,7 @@
 	t.Run("Invalid JSON Input", func(t *testing.T) {
 		input := json.RawMessage(`{"command":123}`) // Invalid JSON (command must be string)
 
-		_, err := Bash.Run(context.Background(), input)
+		_, err := tool.Run(context.Background(), input)
 		if err == nil {
 			t.Errorf("Expected error for invalid input, got none")
 		}
@@ -117,10 +166,9 @@
 	t.Run("Successful Command", func(t *testing.T) {
 		req := bashInput{
 			Command: "echo 'Success'",
-			Timeout: "5s",
 		}
 
-		output, err := executeBash(ctx, req)
+		output, err := executeBash(ctx, req, 5*time.Second)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -135,10 +183,9 @@
 	t.Run("SKETCH Environment Variable", func(t *testing.T) {
 		req := bashInput{
 			Command: "echo $SKETCH",
-			Timeout: "5s",
 		}
 
-		output, err := executeBash(ctx, req)
+		output, err := executeBash(ctx, req, 5*time.Second)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -153,10 +200,9 @@
 	t.Run("Command with stderr", func(t *testing.T) {
 		req := bashInput{
 			Command: "echo 'Error message' >&2 && echo 'Success'",
-			Timeout: "5s",
 		}
 
-		output, err := executeBash(ctx, req)
+		output, err := executeBash(ctx, req, 5*time.Second)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -171,10 +217,9 @@
 	t.Run("Failed Command with stderr", func(t *testing.T) {
 		req := bashInput{
 			Command: "echo 'Error message' >&2 && exit 1",
-			Timeout: "5s",
 		}
 
-		_, err := executeBash(ctx, req)
+		_, err := executeBash(ctx, req, 5*time.Second)
 		if err == nil {
 			t.Errorf("Expected error for failed command, got none")
 		} else if !strings.Contains(err.Error(), "Error message") {
@@ -186,11 +231,10 @@
 	t.Run("Command Timeout", func(t *testing.T) {
 		req := bashInput{
 			Command: "sleep 1 && echo 'Should not see this'",
-			Timeout: "100ms",
 		}
 
 		start := time.Now()
-		_, err := executeBash(ctx, req)
+		_, err := executeBash(ctx, req, 100*time.Millisecond)
 		elapsed := time.Since(start)
 
 		// Command should time out after ~100ms, not wait for full 1 second
@@ -207,6 +251,9 @@
 }
 
 func TestBackgroundBash(t *testing.T) {
+	var bashTool BashTool
+	tool := bashTool.Tool()
+
 	// Test basic background execution
 	t.Run("Basic Background Command", func(t *testing.T) {
 		inputObj := struct {
@@ -221,7 +268,7 @@
 			t.Fatalf("Failed to marshal input: %v", err)
 		}
 
-		result, err := Bash.Run(context.Background(), inputJSON)
+		result, err := tool.Run(context.Background(), inputJSON)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -279,7 +326,7 @@
 			t.Fatalf("Failed to marshal input: %v", err)
 		}
 
-		result, err := Bash.Run(context.Background(), inputJSON)
+		result, err := tool.Run(context.Background(), inputJSON)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -337,7 +384,7 @@
 		}
 
 		// Start the command in the background
-		result, err := Bash.Run(context.Background(), inputJSON)
+		result, err := tool.Run(context.Background(), inputJSON)
 		if err != nil {
 			t.Fatalf("Unexpected error: %v", err)
 		}
@@ -390,8 +437,8 @@
 			Command:    "echo 'test'",
 			Background: false,
 		}
-		fgTimeout := foreground.timeout()
-		expectedFg := 10 * time.Second
+		fgTimeout := foreground.timeout(nil)
+		expectedFg := 30 * time.Second
 		if fgTimeout != expectedFg {
 			t.Errorf("Expected foreground default timeout to be %v, got %v", expectedFg, fgTimeout)
 		}
@@ -401,22 +448,38 @@
 			Command:    "echo 'test'",
 			Background: true,
 		}
-		bgTimeout := background.timeout()
-		expectedBg := 10 * time.Minute
+		bgTimeout := background.timeout(nil)
+		expectedBg := 24 * time.Hour
 		if bgTimeout != expectedBg {
 			t.Errorf("Expected background default timeout to be %v, got %v", expectedBg, bgTimeout)
 		}
 
-		// Test explicit timeout overrides defaults
-		explicit := bashInput{
+		// Test slow_ok timeout
+		slowOk := bashInput{
 			Command:    "echo 'test'",
-			Background: true,
-			Timeout:    "5s",
+			Background: false,
+			SlowOK:     true,
 		}
-		explicitTimeout := explicit.timeout()
-		expectedExplicit := 5 * time.Second
-		if explicitTimeout != expectedExplicit {
-			t.Errorf("Expected explicit timeout to be %v, got %v", expectedExplicit, explicitTimeout)
+		slowTimeout := slowOk.timeout(nil)
+		expectedSlow := 15 * time.Minute
+		if slowTimeout != expectedSlow {
+			t.Errorf("Expected slow_ok timeout to be %v, got %v", expectedSlow, slowTimeout)
+		}
+
+		// Test custom timeout config
+		customTimeouts := &Timeouts{
+			Fast:       5 * time.Second,
+			Slow:       2 * time.Minute,
+			Background: 1 * time.Hour,
+		}
+		customFast := bashInput{
+			Command:    "echo 'test'",
+			Background: false,
+		}
+		customTimeout := customFast.timeout(customTimeouts)
+		expectedCustom := 5 * time.Second
+		if customTimeout != expectedCustom {
+			t.Errorf("Expected custom timeout to be %v, got %v", expectedCustom, customTimeout)
 		}
 	})
 }