diff --git a/cmd/cmd.go b/cmd/cmd.go
index 3cecbbe2f..f56a1d4b7 100644
--- a/cmd/cmd.go
+++ b/cmd/cmd.go
@@ -520,6 +520,7 @@ func RunHandler(cmd *cobra.Command, args []string) error {
 
 	// Check for experimental flag
 	isExperimental, _ := cmd.Flags().GetBool("experimental")
+	yoloMode, _ := cmd.Flags().GetBool("yolo")
 
 	if interactive {
 		if err := loadOrUnloadModel(cmd, &opts); err != nil {
@@ -547,9 +548,9 @@ func RunHandler(cmd *cobra.Command, args []string) error {
 			}
 		}
 
-		// Use experimental agent loop with
+		// Use experimental agent loop with tools
 		if isExperimental {
-			return xcmd.GenerateInteractive(cmd, opts.Model, opts.WordWrap, opts.Options, opts.Think, opts.HideThinking, opts.KeepAlive)
+			return xcmd.GenerateInteractive(cmd, opts.Model, opts.WordWrap, opts.Options, opts.Think, opts.HideThinking, opts.KeepAlive, yoloMode)
 		}
 
 		return generateInteractive(cmd, opts)
@@ -1764,6 +1765,7 @@ func NewCLI() *cobra.Command {
 	runCmd.Flags().Bool("truncate", false, "For embedding models: truncate inputs exceeding context length (default: true). Set --truncate=false to error instead")
 	runCmd.Flags().Int("dimensions", 0, "Truncate output embeddings to specified dimension (embedding models only)")
 	runCmd.Flags().Bool("experimental", false, "Enable experimental agent loop with tools")
+	runCmd.Flags().BoolP("yolo", "y", false, "Skip all tool approval prompts (use with caution)")
 
 	stopCmd := &cobra.Command{
 		Use:     "stop MODEL",
diff --git a/readline/errors.go b/readline/errors.go
index bb3fbd473..83c26e86e 100644
--- a/readline/errors.go
+++ b/readline/errors.go
@@ -6,6 +6,9 @@ import (
 
 var ErrInterrupt = errors.New("Interrupt")
 
+// ErrExpandOutput is returned when user presses Ctrl+O to expand tool output
+var ErrExpandOutput = errors.New("ExpandOutput")
+
 type InterruptError struct {
 	Line []rune
 }
diff --git a/readline/readline.go b/readline/readline.go
index c12327472..8bbef66fd 100644
--- a/readline/readline.go
+++ b/readline/readline.go
@@ -206,6 +206,9 @@ func (i *Instance) Readline() (string, error) {
 			buf.DeleteBefore()
 		case CharCtrlL:
 			buf.ClearScreen()
+		case CharCtrlO:
+			// Ctrl+O - expand tool output
+			return "", ErrExpandOutput
 		case CharCtrlW:
 			buf.DeleteWord()
 		case CharCtrlZ:
diff --git a/readline/types.go b/readline/types.go
index f4efa8d92..f1509f63f 100644
--- a/readline/types.go
+++ b/readline/types.go
@@ -18,6 +18,7 @@ const (
 	CharCtrlL     = 12
 	CharEnter     = 13
 	CharNext      = 14
+	CharCtrlO     = 15 // Ctrl+O - used for expanding tool output
 	CharPrev      = 16
 	CharBckSearch = 18
 	CharFwdSearch = 19
diff --git a/x/agent/approval.go b/x/agent/approval.go
index e2d429ac6..3a160e4d9 100644
--- a/x/agent/approval.go
+++ b/x/agent/approval.go
@@ -4,6 +4,7 @@ package agent
 import (
 	"fmt"
 	"os"
+	"path"
 	"path/filepath"
 	"strings"
 	"sync"
@@ -179,6 +180,7 @@ func FormatDeniedResult(command string, pattern string) string {
 // extractBashPrefix extracts a prefix pattern from a bash command.
 // For commands like "cat tools/tools_test.go | head -200", returns "cat:tools/"
 // For commands without path args, returns empty string.
+// Paths with ".." traversal that escape the base directory return empty string for security.
 func extractBashPrefix(command string) string {
 	// Split command by pipes and get the first part
 	parts := strings.Split(command, "|")
@@ -204,8 +206,8 @@ func extractBashPrefix(command string) string {
 		return ""
 	}
 
-	// Find the first path-like argument (must contain / or start with .)
-	// First pass: look for clear paths (containing / or starting with .)
+	// Find the first path-like argument (must contain / or \ or start with .)
+	// First pass: look for clear paths (containing path separators or starting with .)
 	for _, arg := range fields[1:] {
 		// Skip flags
 		if strings.HasPrefix(arg, "-") {
@@ -215,19 +217,49 @@ func extractBashPrefix(command string) string {
 		if isNumeric(arg) {
 			continue
 		}
-		// Only process if it looks like a path (contains / or starts with .)
-		if !strings.Contains(arg, "/") && !strings.HasPrefix(arg, ".") {
+		// Only process if it looks like a path (contains / or \ or starts with .)
+		if !strings.Contains(arg, "/") && !strings.Contains(arg, "\\") && !strings.HasPrefix(arg, ".") {
 			continue
 		}
-		// If arg ends with /, it's a directory - use it directly
-		if strings.HasSuffix(arg, "/") {
-			return fmt.Sprintf("%s:%s", baseCmd, arg)
+		// Normalize to forward slashes for consistent cross-platform matching
+		arg = strings.ReplaceAll(arg, "\\", "/")
+
+		// Security: reject absolute paths
+		if path.IsAbs(arg) {
+			return "" // Absolute path - don't create prefix
 		}
-		// Get the directory part of a file path
-		dir := filepath.Dir(arg)
+
+		// Normalize the path using stdlib path.Clean (resolves . and ..)
+		cleaned := path.Clean(arg)
+
+		// Security: reject if cleaned path escapes to parent directory
+		if strings.HasPrefix(cleaned, "..") {
+			return "" // Path escapes - don't create prefix
+		}
+
+		// Security: if original had "..", verify cleaned path didn't escape to sibling
+		// e.g., "tools/a/b/../../../etc" -> "etc" (escaped tools/ to sibling)
+		if strings.Contains(arg, "..") {
+			origBase := strings.SplitN(arg, "/", 2)[0]
+			cleanedBase := strings.SplitN(cleaned, "/", 2)[0]
+			if origBase != cleanedBase {
+				return "" // Path escaped to sibling directory
+			}
+		}
+
+		// Check if arg ends with / (explicit directory)
+		isDir := strings.HasSuffix(arg, "/")
+
+		// Get the directory part
+		var dir string
+		if isDir {
+			dir = cleaned
+		} else {
+			dir = path.Dir(cleaned)
+		}
+
 		if dir == "." {
-			// Path is just a directory like "tools" or "src" (no trailing /)
-			return fmt.Sprintf("%s:%s/", baseCmd, arg)
+			return fmt.Sprintf("%s:./", baseCmd)
 		}
 		return fmt.Sprintf("%s:%s/", baseCmd, dir)
 	}
@@ -332,6 +364,8 @@ func AllowlistKey(toolName string, args map[string]any) string {
 }
 
 // IsAllowed checks if a tool/command is allowed (exact match or prefix match).
+// For bash commands, hierarchical path matching is used - if "cat:tools/" is allowed,
+// then "cat:tools/subdir/" is also allowed (subdirectories inherit parent permissions).
 func (a *ApprovalManager) IsAllowed(toolName string, args map[string]any) bool {
 	a.mu.RLock()
 	defer a.mu.RUnlock()
@@ -342,12 +376,20 @@ func (a *ApprovalManager) IsAllowed(toolName string, args map[string]any) bool {
 		return true
 	}
 
-	// For bash commands, check prefix matches
+	// For bash commands, check prefix matches with hierarchical path support
 	if toolName == "bash" {
 		if cmd, ok := args["command"].(string); ok {
 			prefix := extractBashPrefix(cmd)
-			if prefix != "" && a.prefixes[prefix] {
-				return true
+			if prefix != "" {
+				// Check exact prefix match first
+				if a.prefixes[prefix] {
+					return true
+				}
+				// Check hierarchical match: if any stored prefix is a parent of current prefix
+				// e.g., stored "cat:tools/" should match current "cat:tools/subdir/"
+				if a.matchesHierarchicalPrefix(prefix) {
+					return true
+				}
 			}
 		}
 	}
@@ -360,6 +402,40 @@ func (a *ApprovalManager) IsAllowed(toolName string, args map[string]any) bool {
 	return false
 }
 
+// matchesHierarchicalPrefix checks if the given prefix matches any stored prefix hierarchically.
+// For example, if "cat:tools/" is stored, it will match "cat:tools/subdir/" or "cat:tools/a/b/c/".
+func (a *ApprovalManager) matchesHierarchicalPrefix(currentPrefix string) bool {
+	// Split prefix into command and path parts (format: "cmd:path/")
+	colonIdx := strings.Index(currentPrefix, ":")
+	if colonIdx == -1 {
+		return false
+	}
+	currentCmd := currentPrefix[:colonIdx]
+	currentPath := currentPrefix[colonIdx+1:]
+
+	for storedPrefix := range a.prefixes {
+		storedColonIdx := strings.Index(storedPrefix, ":")
+		if storedColonIdx == -1 {
+			continue
+		}
+		storedCmd := storedPrefix[:storedColonIdx]
+		storedPath := storedPrefix[storedColonIdx+1:]
+
+		// Commands must match exactly
+		if currentCmd != storedCmd {
+			continue
+		}
+
+		// Check if current path starts with stored path (hierarchical match)
+		// e.g., "tools/subdir/" starts with "tools/"
+		if strings.HasPrefix(currentPath, storedPath) {
+			return true
+		}
+	}
+
+	return false
+}
+
 // AddToAllowlist adds a tool/command to the session allowlist.
 // For bash commands, it adds the prefix pattern instead of exact command.
 func (a *ApprovalManager) AddToAllowlist(toolName string, args map[string]any) {
@@ -443,11 +519,12 @@ func formatToolDisplay(toolName string, args map[string]any) string {
 		}
 	}
 
-	// For web search, show query
+	// For web search, show query and internet notice
 	if toolName == "web_search" {
 		if query, ok := args["query"].(string); ok {
 			sb.WriteString(fmt.Sprintf("Tool: %s\n", toolName))
-			sb.WriteString(fmt.Sprintf("Query: %s", query))
+			sb.WriteString(fmt.Sprintf("Query: %s\n", query))
+			sb.WriteString("Uses internet via ollama.com")
 			return sb.String()
 		}
 	}
@@ -951,3 +1028,79 @@ func FormatDenyResult(toolName string, reason string) string {
 	}
 	return fmt.Sprintf("User denied execution of %s.", toolName)
 }
+
+// PromptYesNo displays a simple Yes/No prompt and returns the user's choice.
+// Returns true for Yes, false for No.
+func PromptYesNo(question string) (bool, error) {
+	fd := int(os.Stdin.Fd())
+	oldState, err := term.MakeRaw(fd)
+	if err != nil {
+		return false, err
+	}
+	defer term.Restore(fd, oldState)
+
+	selected := 0 // 0 = Yes, 1 = No
+	options := []string{"Yes", "No"}
+
+	// Hide cursor
+	fmt.Fprint(os.Stderr, "\033[?25l")
+	defer fmt.Fprint(os.Stderr, "\033[?25h")
+
+	renderYesNo := func() {
+		// Move to start of line and clear
+		fmt.Fprintf(os.Stderr, "\r\033[K")
+		fmt.Fprintf(os.Stderr, "\033[36m%s\033[0m ", question)
+		for i, opt := range options {
+			if i == selected {
+				fmt.Fprintf(os.Stderr, "\033[1;32m[%s]\033[0m ", opt)
+			} else {
+				fmt.Fprintf(os.Stderr, "\033[90m %s \033[0m ", opt)
+			}
+		}
+		fmt.Fprintf(os.Stderr, "\033[90m(←/→ or y/n, Enter to confirm)\033[0m")
+	}
+
+	renderYesNo()
+
+	buf := make([]byte, 3)
+	for {
+		n, err := os.Stdin.Read(buf)
+		if err != nil {
+			return false, err
+		}
+
+		if n == 1 {
+			switch buf[0] {
+			case 'y', 'Y':
+				selected = 0
+				renderYesNo()
+			case 'n', 'N':
+				selected = 1
+				renderYesNo()
+			case '\r', '\n': // Enter
+				fmt.Fprintf(os.Stderr, "\r\033[K") // Clear line
+				return selected == 0, nil
+			case 3: // Ctrl+C
+				fmt.Fprintf(os.Stderr, "\r\033[K")
+				return false, nil
+			case 27: // Escape - could be arrow key
+				// Read more bytes for arrow keys
+				continue
+			}
+		} else if n == 3 && buf[0] == 27 && buf[1] == 91 {
+			// Arrow keys
+			switch buf[2] {
+			case 'D': // Left
+				if selected > 0 {
+					selected--
+				}
+				renderYesNo()
+			case 'C': // Right
+				if selected < len(options)-1 {
+					selected++
+				}
+				renderYesNo()
+			}
+		}
+	}
+}
diff --git a/x/agent/approval_test.go b/x/agent/approval_test.go
index 652ca8c3b..a05ea3d42 100644
--- a/x/agent/approval_test.go
+++ b/x/agent/approval_test.go
@@ -151,6 +151,27 @@ func TestExtractBashPrefix(t *testing.T) {
 			command:  "head -n 100",
 			expected: "",
 		},
+		// Path traversal security tests
+		{
+			name:     "path traversal - parent escape",
+			command:  "cat tools/../../etc/passwd",
+			expected: "", // Should NOT create a prefix - path escapes
+		},
+		{
+			name:     "path traversal - deep escape",
+			command:  "cat tools/a/b/../../../etc/passwd",
+			expected: "", // Normalizes to "../etc/passwd" - escapes
+		},
+		{
+			name:     "path traversal - absolute path",
+			command:  "cat /etc/passwd",
+			expected: "", // Absolute paths should not create prefix
+		},
+		{
+			name:     "path with safe dotdot - normalized",
+			command:  "cat tools/subdir/../file.go",
+			expected: "cat:tools/", // Normalizes to tools/file.go - safe, creates prefix
+		},
 	}
 
 	for _, tt := range tests {
@@ -164,6 +185,34 @@ func TestExtractBashPrefix(t *testing.T) {
 	}
 }
 
+func TestApprovalManager_PathTraversalBlocked(t *testing.T) {
+	am := NewApprovalManager()
+
+	// Allow "cat tools/file.go" - creates prefix "cat:tools/"
+	am.AddToAllowlist("bash", map[string]any{"command": "cat tools/file.go"})
+
+	// Path traversal attack: should NOT be allowed
+	if am.IsAllowed("bash", map[string]any{"command": "cat tools/../../etc/passwd"}) {
+		t.Error("SECURITY: path traversal attack should NOT be allowed")
+	}
+
+	// Another traversal variant
+	if am.IsAllowed("bash", map[string]any{"command": "cat tools/../../../etc/shadow"}) {
+		t.Error("SECURITY: deep path traversal should NOT be allowed")
+	}
+
+	// Valid subdirectory access should still work
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools/subdir/file.go"}) {
+		t.Error("expected cat tools/subdir/file.go to be allowed")
+	}
+
+	// Safe ".." that normalizes to within allowed directory should work
+	// tools/subdir/../other.go normalizes to tools/other.go which is under tools/
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools/subdir/../other.go"}) {
+		t.Error("expected cat tools/subdir/../other.go to be allowed (normalizes to tools/other.go)")
+	}
+}
+
 func TestApprovalManager_PrefixAllowlist(t *testing.T) {
 	am := NewApprovalManager()
 
@@ -186,6 +235,119 @@ func TestApprovalManager_PrefixAllowlist(t *testing.T) {
 	}
 }
 
+func TestApprovalManager_HierarchicalPrefixAllowlist(t *testing.T) {
+	am := NewApprovalManager()
+
+	// Allow "cat tools/file.go" - this creates prefix "cat:tools/"
+	am.AddToAllowlist("bash", map[string]any{"command": "cat tools/file.go"})
+
+	// Should allow subdirectories (hierarchical matching)
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools/subdir/file.go"}) {
+		t.Error("expected cat tools/subdir/file.go to be allowed via hierarchical prefix")
+	}
+
+	// Should allow deeply nested subdirectories
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools/a/b/c/deep.go"}) {
+		t.Error("expected cat tools/a/b/c/deep.go to be allowed via hierarchical prefix")
+	}
+
+	// Should still allow same directory
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools/another.go"}) {
+		t.Error("expected cat tools/another.go to be allowed")
+	}
+
+	// Should NOT allow different base directory
+	if am.IsAllowed("bash", map[string]any{"command": "cat src/main.go"}) {
+		t.Error("expected cat src/main.go to NOT be allowed")
+	}
+
+	// Should NOT allow different command even in subdirectory
+	if am.IsAllowed("bash", map[string]any{"command": "ls tools/subdir/"}) {
+		t.Error("expected ls tools/subdir/ to NOT be allowed (different command)")
+	}
+
+	// Should NOT allow similar but different directory name
+	if am.IsAllowed("bash", map[string]any{"command": "cat toolsbin/file.go"}) {
+		t.Error("expected cat toolsbin/file.go to NOT be allowed (different directory)")
+	}
+}
+
+func TestApprovalManager_HierarchicalPrefixAllowlist_CrossPlatform(t *testing.T) {
+	am := NewApprovalManager()
+
+	// Allow with forward slashes (Unix-style)
+	am.AddToAllowlist("bash", map[string]any{"command": "cat tools/file.go"})
+
+	// Should work with backslashes too (Windows-style) - normalized internally
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools\\subdir\\file.go"}) {
+		t.Error("expected cat tools\\subdir\\file.go to be allowed via hierarchical prefix (Windows path)")
+	}
+
+	// Mixed slashes should also work
+	if !am.IsAllowed("bash", map[string]any{"command": "cat tools\\a/b\\c/deep.go"}) {
+		t.Error("expected mixed slash path to be allowed via hierarchical prefix")
+	}
+}
+
+func TestMatchesHierarchicalPrefix(t *testing.T) {
+	am := NewApprovalManager()
+
+	// Add prefix for "cat:tools/"
+	am.prefixes["cat:tools/"] = true
+
+	tests := []struct {
+		name     string
+		prefix   string
+		expected bool
+	}{
+		{
+			name:     "exact match",
+			prefix:   "cat:tools/",
+			expected: true, // exact match also passes HasPrefix - caller handles exact match first
+		},
+		{
+			name:     "subdirectory",
+			prefix:   "cat:tools/subdir/",
+			expected: true,
+		},
+		{
+			name:     "deeply nested",
+			prefix:   "cat:tools/a/b/c/",
+			expected: true,
+		},
+		{
+			name:     "different base directory",
+			prefix:   "cat:src/",
+			expected: false,
+		},
+		{
+			name:     "different command same path",
+			prefix:   "ls:tools/",
+			expected: false,
+		},
+		{
+			name:     "similar directory name",
+			prefix:   "cat:toolsbin/",
+			expected: false,
+		},
+		{
+			name:     "invalid prefix format",
+			prefix:   "cattools",
+			expected: false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := am.matchesHierarchicalPrefix(tt.prefix)
+			if result != tt.expected {
+				t.Errorf("matchesHierarchicalPrefix(%q) = %v, expected %v",
+					tt.prefix, result, tt.expected)
+			}
+		})
+	}
+}
+
 func TestFormatApprovalResult(t *testing.T) {
 	tests := []struct {
 		name     string
diff --git a/x/cmd/run.go b/x/cmd/run.go
index 2a76a5592..178659e9f 100644
--- a/x/cmd/run.go
+++ b/x/cmd/run.go
@@ -6,10 +6,12 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"net/url"
 	"os"
 	"os/signal"
 	"strings"
 	"syscall"
+	"time"
 
 	"github.com/spf13/cobra"
 	"golang.org/x/term"
@@ -22,6 +24,101 @@ import (
 	"github.com/ollama/ollama/x/tools"
 )
 
+// Tool output capping constants
+const (
+	// localModelTokenLimit is the token limit for local models (smaller context).
+	localModelTokenLimit = 4000
+
+	// defaultTokenLimit is the token limit for cloud/remote models.
+	defaultTokenLimit = 10000
+
+	// charsPerToken is a rough estimate of characters per token.
+	// TODO: Estimate tokens more accurately using tokenizer if available
+	charsPerToken = 4
+)
+
+// isLocalModel checks if the model is running locally (not a cloud model).
+// TODO: Improve local/cloud model identification - could check model metadata
+func isLocalModel(modelName string) bool {
+	return !strings.HasSuffix(modelName, "-cloud")
+}
+
+// isLocalServer checks if connecting to a local Ollama server.
+// TODO: Could also check other indicators of local vs cloud server
+func isLocalServer() bool {
+	host := os.Getenv("OLLAMA_HOST")
+	if host == "" {
+		return true // Default is localhost:11434
+	}
+
+	// Parse the URL to check host
+	parsed, err := url.Parse(host)
+	if err != nil {
+		return true // If can't parse, assume local
+	}
+
+	hostname := parsed.Hostname()
+	return hostname == "localhost" || hostname == "127.0.0.1" || strings.Contains(parsed.Host, ":11434")
+}
+
+// truncateToolOutput truncates tool output to prevent context overflow.
+// Uses a smaller limit (4k tokens) for local models, larger (10k) for cloud/remote.
+func truncateToolOutput(output, modelName string) string {
+	var tokenLimit int
+	if isLocalModel(modelName) && isLocalServer() {
+		tokenLimit = localModelTokenLimit
+	} else {
+		tokenLimit = defaultTokenLimit
+	}
+
+	maxChars := tokenLimit * charsPerToken
+	if len(output) > maxChars {
+		return output[:maxChars] + "\n... (output truncated)"
+	}
+	return output
+}
+
+// waitForOllamaSignin shows the signin URL and polls until authentication completes.
+func waitForOllamaSignin(ctx context.Context) error {
+	client, err := api.ClientFromEnvironment()
+	if err != nil {
+		return err
+	}
+
+	// Get signin URL from initial Whoami call
+	_, err = client.Whoami(ctx)
+	if err != nil {
+		var aErr api.AuthorizationError
+		if errors.As(err, &aErr) && aErr.SigninURL != "" {
+			fmt.Fprintf(os.Stderr, "\n  To sign in, navigate to:\n")
+			fmt.Fprintf(os.Stderr, "      \033[36m%s\033[0m\n\n", aErr.SigninURL)
+			fmt.Fprintf(os.Stderr, "  \033[90mWaiting for sign in to complete...\033[0m")
+
+			// Poll until auth succeeds
+			ticker := time.NewTicker(2 * time.Second)
+			defer ticker.Stop()
+
+			for {
+				select {
+				case <-ctx.Done():
+					fmt.Fprintf(os.Stderr, "\n")
+					return ctx.Err()
+				case <-ticker.C:
+					user, whoamiErr := client.Whoami(ctx)
+					if whoamiErr == nil && user != nil && user.Name != "" {
+						fmt.Fprintf(os.Stderr, "\r\033[K  \033[32mSigned in as %s\033[0m\n", user.Name)
+						return nil
+					}
+					// Still waiting, show dot
+					fmt.Fprintf(os.Stderr, ".")
+				}
+			}
+		}
+		return err
+	}
+	return nil
+}
+
 // RunOptions contains options for running an interactive agent session.
 type RunOptions struct {
 	Model        string
@@ -37,6 +134,16 @@ type RunOptions struct {
 	// Agent fields (managed externally for session persistence)
 	Tools    *tools.Registry
 	Approval *agent.ApprovalManager
+
+	// YoloMode skips all tool approval prompts
+	YoloMode bool
+
+	// LastToolOutput stores the full output of the last tool execution
+	// for Ctrl+O expansion. Updated by Chat(), read by caller.
+	LastToolOutput *string
+
+	// LastToolOutputTruncated stores the truncated version shown inline
+	LastToolOutputTruncated *string
 }
 
 // Chat runs an agent chat loop with tool support.
@@ -77,6 +184,7 @@ func Chat(ctx context.Context, opts RunOptions) (*api.Message, error) {
 	var thinkTagOpened bool = false
 	var thinkTagClosed bool = false
 	var pendingToolCalls []api.ToolCall
+	var consecutiveErrors int // Track consecutive 500 errors for retry limit
 
 	role := "assistant"
 	messages := opts.Messages
@@ -159,6 +267,58 @@ func Chat(ctx context.Context, opts RunOptions) (*api.Message, error) {
 				return nil, nil
 			}
 
+			// Check for 401 Unauthorized - prompt user to sign in
+			var authErr api.AuthorizationError
+			if errors.As(err, &authErr) {
+				p.StopAndClear()
+				fmt.Fprintf(os.Stderr, "\033[33mAuthentication required to use this cloud model.\033[0m\n")
+				result, promptErr := agent.PromptYesNo("Sign in to Ollama?")
+				if promptErr == nil && result {
+					if signinErr := waitForOllamaSignin(ctx); signinErr == nil {
+						// Retry the chat request
+						fmt.Fprintf(os.Stderr, "\033[90mRetrying...\033[0m\n")
+						continue // Retry the loop
+					}
+				}
+				return nil, fmt.Errorf("authentication required - run 'ollama signin' to authenticate")
+			}
+
+			// Check for 500 errors (often tool parsing failures) - inform the model
+			var statusErr api.StatusError
+			if errors.As(err, &statusErr) && statusErr.StatusCode >= 500 {
+				consecutiveErrors++
+				p.StopAndClear()
+
+				if consecutiveErrors >= 3 {
+					fmt.Fprintf(os.Stderr, "\033[31m✗ Too many consecutive errors, giving up\033[0m\n")
+					return nil, fmt.Errorf("too many consecutive server errors: %s", statusErr.ErrorMessage)
+				}
+
+				fmt.Fprintf(os.Stderr, "\033[33m⚠ Server error (attempt %d/3): %s\033[0m\n", consecutiveErrors, statusErr.ErrorMessage)
+
+				// Include both the model's response and the error so it can learn
+				assistantContent := fullResponse.String()
+				if assistantContent == "" {
+					assistantContent = "(empty response)"
+				}
+				errorMsg := fmt.Sprintf("Your previous response caused an error: %s\n\nYour response was:\n%s\n\nPlease try again with a valid response.", statusErr.ErrorMessage, assistantContent)
+				messages = append(messages,
+					api.Message{Role: "user", Content: errorMsg},
+				)
+
+				// Reset state and retry
+				fullResponse.Reset()
+				thinkingContent.Reset()
+				thinkTagOpened = false
+				thinkTagClosed = false
+				pendingToolCalls = nil
+				state = &displayResponseState{}
+				p = progress.NewProgress(os.Stderr)
+				spinner = progress.NewSpinner("")
+				p.Add("", spinner)
+				continue
+			}
+
 			if strings.Contains(err.Error(), "upstream error") {
 				p.StopAndClear()
 				fmt.Println("An error occurred while processing your message. Please try again.")
@@ -168,6 +328,9 @@ func Chat(ctx context.Context, opts RunOptions) (*api.Message, error) {
 			return nil, err
 		}
 
+		// Reset consecutive error counter on success
+		consecutiveErrors = 0
+
 		// If no tool calls, we're done
 		if len(pendingToolCalls) == 0 || toolRegistry == nil {
 			break
@@ -216,7 +379,12 @@ func Chat(ctx context.Context, opts RunOptions) (*api.Message, error) {
 			}
 
 			// Check approval (uses prefix matching for bash commands)
-			if !skipApproval && !approval.IsAllowed(toolName, args) {
+			// In yolo mode, skip all approval prompts
+			if opts.YoloMode {
+				if !skipApproval {
+					fmt.Fprintf(os.Stderr, "\033[90m▶ Running: %s\033[0m\n", formatToolShort(toolName, args))
+				}
+			} else if !skipApproval && !approval.IsAllowed(toolName, args) {
 				result, err := approval.RequestApproval(toolName, args)
 				if err != nil {
 					fmt.Fprintf(os.Stderr, "Error requesting approval: %v\n", err)
@@ -250,6 +418,23 @@ func Chat(ctx context.Context, opts RunOptions) (*api.Message, error) {
 			// Execute the tool
 			toolResult, err := toolRegistry.Execute(call)
 			if err != nil {
+				// Check if web search needs authentication
+				if errors.Is(err, tools.ErrWebSearchAuthRequired) {
+					// Prompt user to sign in
+					fmt.Fprintf(os.Stderr, "\033[33m  Web search requires authentication.\033[0m\n")
+					result, promptErr := agent.PromptYesNo("Sign in to Ollama?")
+					if promptErr == nil && result {
+						// Get signin URL and wait for auth completion
+						if signinErr := waitForOllamaSignin(ctx); signinErr == nil {
+							// Retry the web search
+							fmt.Fprintf(os.Stderr, "\033[90m  Retrying web search...\033[0m\n")
+							toolResult, err = toolRegistry.Execute(call)
+							if err == nil {
+								goto toolSuccess
+							}
+						}
+					}
+				}
 				fmt.Fprintf(os.Stderr, "\033[31m  Error: %v\033[0m\n", err)
 				toolResults = append(toolResults, api.Message{
 					Role:       "tool",
@@ -258,20 +443,34 @@ func Chat(ctx context.Context, opts RunOptions) (*api.Message, error) {
 				})
 				continue
 			}
+		toolSuccess:
 
 			// Display tool output (truncated for display)
+			truncatedOutput := ""
 			if toolResult != "" {
 				output := toolResult
 				if len(output) > 300 {
-					output = output[:300] + "... (truncated)"
+					output = output[:300] + "... (truncated, press Ctrl+O to expand)"
 				}
+				truncatedOutput = output
 				// Show result in grey, indented
 				fmt.Fprintf(os.Stderr, "\033[90m  %s\033[0m\n", strings.ReplaceAll(output, "\n", "\n  "))
 			}
 
+			// Store full and truncated output for Ctrl+O toggle
+			if opts.LastToolOutput != nil {
+				*opts.LastToolOutput = toolResult
+			}
+			if opts.LastToolOutputTruncated != nil {
+				*opts.LastToolOutputTruncated = truncatedOutput
+			}
+
+			// Truncate output to prevent context overflow
+			toolResultForLLM := truncateToolOutput(toolResult, opts.Model)
+
 			toolResults = append(toolResults, api.Message{
 				Role:       "tool",
-				Content:    toolResult,
+				Content:    toolResultForLLM,
 				ToolCallID: call.ID,
 			})
 		}
@@ -449,7 +648,8 @@ func checkModelCapabilities(ctx context.Context, modelName string) (supportsTool
 
 // GenerateInteractive runs an interactive agent session.
 // This is called from cmd.go when --experimental flag is set.
-func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, options map[string]any, think *api.ThinkValue, hideThinking bool, keepAlive *api.Duration) error {
+// If yoloMode is true, all tool approvals are skipped.
+func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, options map[string]any, think *api.ThinkValue, hideThinking bool, keepAlive *api.Duration, yoloMode bool) error {
 	scanner, err := readline.New(readline.Prompt{
 		Prompt:         ">>> ",
 		AltPrompt:      "... ",
@@ -474,11 +674,11 @@ func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, op
 	var toolRegistry *tools.Registry
 	if supportsTools {
 		toolRegistry = tools.DefaultRegistry()
-		fmt.Fprintf(os.Stderr, "Tools available: %s\n", strings.Join(toolRegistry.Names(), ", "))
-
-		// Check for OLLAMA_API_KEY for web search
-		if os.Getenv("OLLAMA_API_KEY") == "" {
-			fmt.Fprintf(os.Stderr, "\033[33mWarning: OLLAMA_API_KEY not set - web search will not work\033[0m\n")
+		if toolRegistry.Count() > 0 {
+			fmt.Fprintf(os.Stderr, "\033[90mTools available: %s\033[0m\n", strings.Join(toolRegistry.Names(), ", "))
+		}
+		if yoloMode {
+			fmt.Fprintf(os.Stderr, "\033[33m⚠ YOLO mode: All tool approvals will be skipped\033[0m\n")
 		}
 	} else {
 		fmt.Fprintf(os.Stderr, "\033[33mNote: Model does not support tools - running in chat-only mode\033[0m\n")
@@ -490,6 +690,11 @@ func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, op
 	var messages []api.Message
 	var sb strings.Builder
 
+	// Track last tool output for Ctrl+O toggle
+	var lastToolOutput string
+	var lastToolOutputTruncated string
+	var toolOutputExpanded bool
+
 	for {
 		line, err := scanner.Readline()
 		switch {
@@ -502,6 +707,20 @@ func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, op
 			}
 			sb.Reset()
 			continue
+		case errors.Is(err, readline.ErrExpandOutput):
+			// Ctrl+O pressed - toggle between expanded and collapsed tool output
+			if lastToolOutput == "" {
+				fmt.Fprintf(os.Stderr, "\033[90mNo tool output to expand\033[0m\n")
+			} else if toolOutputExpanded {
+				// Currently expanded, show truncated
+				fmt.Fprintf(os.Stderr, "\033[90m  %s\033[0m\n", strings.ReplaceAll(lastToolOutputTruncated, "\n", "\n  "))
+				toolOutputExpanded = false
+			} else {
+				// Currently collapsed, show full
+				fmt.Fprintf(os.Stderr, "\033[90m  %s\033[0m\n", strings.ReplaceAll(lastToolOutput, "\n", "\n  "))
+				toolOutputExpanded = true
+			}
+			continue
 		case err != nil:
 			return err
 		}
@@ -524,6 +743,9 @@ func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, op
 			fmt.Fprintln(os.Stderr, "  /bye            Exit")
 			fmt.Fprintln(os.Stderr, "  /?, /help       Help for a command")
 			fmt.Fprintln(os.Stderr, "")
+			fmt.Fprintln(os.Stderr, "Keyboard Shortcuts:")
+			fmt.Fprintln(os.Stderr, "  Ctrl+O          Expand last tool output")
+			fmt.Fprintln(os.Stderr, "")
 			continue
 		case strings.HasPrefix(line, "/"):
 			fmt.Printf("Unknown command '%s'. Type /? for help\n", strings.Fields(line)[0])
@@ -537,16 +759,21 @@ func GenerateInteractive(cmd *cobra.Command, modelName string, wordWrap bool, op
 			messages = append(messages, newMessage)
 
 			opts := RunOptions{
-				Model:        modelName,
-				Messages:     messages,
-				WordWrap:     wordWrap,
-				Options:      options,
-				Think:        think,
-				HideThinking: hideThinking,
-				KeepAlive:    keepAlive,
-				Tools:        toolRegistry,
-				Approval:     approval,
+				Model:                   modelName,
+				Messages:                messages,
+				WordWrap:                wordWrap,
+				Options:                 options,
+				Think:                   think,
+				HideThinking:            hideThinking,
+				KeepAlive:               keepAlive,
+				Tools:                   toolRegistry,
+				Approval:                approval,
+				YoloMode:                yoloMode,
+				LastToolOutput:          &lastToolOutput,
+				LastToolOutputTruncated: &lastToolOutputTruncated,
 			}
+			// Reset expanded state for new tool execution
+			toolOutputExpanded = false
 
 			assistant, err := Chat(cmd.Context(), opts)
 			if err != nil {
diff --git a/x/cmd/run_test.go b/x/cmd/run_test.go
new file mode 100644
index 000000000..a65e8cc80
--- /dev/null
+++ b/x/cmd/run_test.go
@@ -0,0 +1,180 @@
+package cmd
+
+import (
+	"testing"
+)
+
+func TestIsLocalModel(t *testing.T) {
+	tests := []struct {
+		name      string
+		modelName string
+		expected  bool
+	}{
+		{
+			name:      "local model without suffix",
+			modelName: "llama3.2",
+			expected:  true,
+		},
+		{
+			name:      "local model with version",
+			modelName: "qwen2.5:7b",
+			expected:  true,
+		},
+		{
+			name:      "cloud model",
+			modelName: "gpt-4-cloud",
+			expected:  false,
+		},
+		{
+			name:      "cloud model with version",
+			modelName: "claude-3-cloud",
+			expected:  false,
+		},
+		{
+			name:      "empty model name",
+			modelName: "",
+			expected:  true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := isLocalModel(tt.modelName)
+			if result != tt.expected {
+				t.Errorf("isLocalModel(%q) = %v, expected %v", tt.modelName, result, tt.expected)
+			}
+		})
+	}
+}
+
+func TestIsLocalServer(t *testing.T) {
+	tests := []struct {
+		name     string
+		host     string
+		expected bool
+	}{
+		{
+			name:     "empty host (default)",
+			host:     "",
+			expected: true,
+		},
+		{
+			name:     "localhost",
+			host:     "http://localhost:11434",
+			expected: true,
+		},
+		{
+			name:     "127.0.0.1",
+			host:     "http://127.0.0.1:11434",
+			expected: true,
+		},
+		{
+			name:     "custom port on localhost",
+			host:     "http://localhost:8080",
+			expected: true, // localhost is always considered local
+		},
+		{
+			name:     "remote host",
+			host:     "http://ollama.example.com:11434",
+			expected: true, // has :11434
+		},
+		{
+			name:     "remote host different port",
+			host:     "http://ollama.example.com:8080",
+			expected: false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Setenv("OLLAMA_HOST", tt.host)
+			result := isLocalServer()
+			if result != tt.expected {
+				t.Errorf("isLocalServer() with OLLAMA_HOST=%q = %v, expected %v", tt.host, result, tt.expected)
+			}
+		})
+	}
+}
+
+func TestTruncateToolOutput(t *testing.T) {
+	// Create outputs of different sizes
+	localLimitOutput := make([]byte, 20000)   // > 4k tokens (16k chars)
+	defaultLimitOutput := make([]byte, 50000) // > 10k tokens (40k chars)
+	for i := range localLimitOutput {
+		localLimitOutput[i] = 'a'
+	}
+	for i := range defaultLimitOutput {
+		defaultLimitOutput[i] = 'b'
+	}
+
+	tests := []struct {
+		name          string
+		output        string
+		modelName     string
+		host          string
+		shouldTrim    bool
+		expectedLimit int
+	}{
+		{
+			name:          "short output local model",
+			output:        "hello world",
+			modelName:     "llama3.2",
+			host:          "",
+			shouldTrim:    false,
+			expectedLimit: localModelTokenLimit,
+		},
+		{
+			name:          "long output local model - trimmed at 4k",
+			output:        string(localLimitOutput),
+			modelName:     "llama3.2",
+			host:          "",
+			shouldTrim:    true,
+			expectedLimit: localModelTokenLimit,
+		},
+		{
+			name:          "long output cloud model - uses 10k limit",
+			output:        string(localLimitOutput), // 20k chars, under 10k token limit
+			modelName:     "gpt-4-cloud",
+			host:          "",
+			shouldTrim:    false,
+			expectedLimit: defaultTokenLimit,
+		},
+		{
+			name:          "very long output cloud model - trimmed at 10k",
+			output:        string(defaultLimitOutput),
+			modelName:     "gpt-4-cloud",
+			host:          "",
+			shouldTrim:    true,
+			expectedLimit: defaultTokenLimit,
+		},
+		{
+			name:          "long output remote server - uses 10k limit",
+			output:        string(localLimitOutput),
+			modelName:     "llama3.2",
+			host:          "http://remote.example.com:8080",
+			shouldTrim:    false,
+			expectedLimit: defaultTokenLimit,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Setenv("OLLAMA_HOST", tt.host)
+			result := truncateToolOutput(tt.output, tt.modelName)
+
+			if tt.shouldTrim {
+				maxLen := tt.expectedLimit * charsPerToken
+				if len(result) > maxLen+50 { // +50 for the truncation message
+					t.Errorf("expected output to be truncated to ~%d chars, got %d", maxLen, len(result))
+				}
+				if result == tt.output {
+					t.Error("expected output to be truncated but it wasn't")
+				}
+			} else {
+				if result != tt.output {
+					t.Error("expected output to not be truncated")
+				}
+			}
+		})
+	}
+}
diff --git a/x/tools/registry.go b/x/tools/registry.go
index f9136c9d7..fba0898b7 100644
--- a/x/tools/registry.go
+++ b/x/tools/registry.go
@@ -3,6 +3,7 @@ package tools
 
 import (
 	"fmt"
+	"os"
 	"sort"
 
 	"github.com/ollama/ollama/api"
@@ -88,9 +89,16 @@ func (r *Registry) Count() int {
 }
 
 // DefaultRegistry creates a registry with all built-in tools.
+// Tools can be disabled via environment variables:
+// - OLLAMA_AGENT_DISABLE_WEBSEARCH=1 disables web_search
+// - OLLAMA_AGENT_DISABLE_BASH=1 disables bash
 func DefaultRegistry() *Registry {
 	r := NewRegistry()
-	r.Register(&WebSearchTool{})
-	r.Register(&BashTool{})
+	if os.Getenv("OLLAMA_AGENT_DISABLE_WEBSEARCH") == "" {
+		r.Register(&WebSearchTool{})
+	}
+	if os.Getenv("OLLAMA_AGENT_DISABLE_BASH") == "" {
+		r.Register(&BashTool{})
+	}
 	return r
 }
diff --git a/x/tools/registry_test.go b/x/tools/registry_test.go
index 59539c721..a37410936 100644
--- a/x/tools/registry_test.go
+++ b/x/tools/registry_test.go
@@ -108,6 +108,57 @@ func TestDefaultRegistry(t *testing.T) {
 	}
 }
 
+func TestDefaultRegistry_DisableWebsearch(t *testing.T) {
+	t.Setenv("OLLAMA_AGENT_DISABLE_WEBSEARCH", "1")
+
+	r := DefaultRegistry()
+
+	if r.Count() != 1 {
+		t.Errorf("expected 1 tool with websearch disabled, got %d", r.Count())
+	}
+
+	_, ok := r.Get("bash")
+	if !ok {
+		t.Error("expected bash tool in registry")
+	}
+
+	_, ok = r.Get("web_search")
+	if ok {
+		t.Error("expected web_search to be disabled")
+	}
+}
+
+func TestDefaultRegistry_DisableBash(t *testing.T) {
+	t.Setenv("OLLAMA_AGENT_DISABLE_BASH", "1")
+
+	r := DefaultRegistry()
+
+	if r.Count() != 1 {
+		t.Errorf("expected 1 tool with bash disabled, got %d", r.Count())
+	}
+
+	_, ok := r.Get("web_search")
+	if !ok {
+		t.Error("expected web_search tool in registry")
+	}
+
+	_, ok = r.Get("bash")
+	if ok {
+		t.Error("expected bash to be disabled")
+	}
+}
+
+func TestDefaultRegistry_DisableBoth(t *testing.T) {
+	t.Setenv("OLLAMA_AGENT_DISABLE_WEBSEARCH", "1")
+	t.Setenv("OLLAMA_AGENT_DISABLE_BASH", "1")
+
+	r := DefaultRegistry()
+
+	if r.Count() != 0 {
+		t.Errorf("expected 0 tools with both disabled, got %d", r.Count())
+	}
+}
+
 func TestBashTool_Schema(t *testing.T) {
 	tool := &BashTool{}
 
diff --git a/x/tools/websearch.go b/x/tools/websearch.go
index 04c3578e1..16b0dde2c 100644
--- a/x/tools/websearch.go
+++ b/x/tools/websearch.go
@@ -2,15 +2,19 @@ package tools
 
 import (
 	"bytes"
+	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io"
 	"net/http"
-	"os"
+	"net/url"
+	"strconv"
 	"strings"
 	"time"
 
 	"github.com/ollama/ollama/api"
+	"github.com/ollama/ollama/auth"
 )
 
 const (
@@ -18,6 +22,9 @@ const (
 	webSearchTimeout = 15 * time.Second
 )
 
+// ErrWebSearchAuthRequired is returned when web search requires authentication
+var ErrWebSearchAuthRequired = errors.New("web search requires authentication")
+
 // WebSearchTool implements web search using Ollama's hosted API.
 type WebSearchTool struct{}
 
@@ -68,17 +75,13 @@ type webSearchResult struct {
 }
 
 // Execute performs the web search.
+// Uses Ollama key signing for authentication - this makes requests via ollama.com API.
 func (w *WebSearchTool) Execute(args map[string]any) (string, error) {
 	query, ok := args["query"].(string)
 	if !ok || query == "" {
 		return "", fmt.Errorf("query parameter is required")
 	}
 
-	apiKey := os.Getenv("OLLAMA_API_KEY")
-	if apiKey == "" {
-		return "", fmt.Errorf("OLLAMA_API_KEY environment variable is required for web search")
-	}
-
 	// Prepare request
 	reqBody := webSearchRequest{
 		Query:      query,
@@ -90,13 +93,34 @@ func (w *WebSearchTool) Execute(args map[string]any) (string, error) {
 		return "", fmt.Errorf("marshaling request: %w", err)
 	}
 
-	req, err := http.NewRequest("POST", webSearchAPI, bytes.NewBuffer(jsonBody))
+	// Parse URL and add timestamp for signing
+	searchURL, err := url.Parse(webSearchAPI)
+	if err != nil {
+		return "", fmt.Errorf("parsing search URL: %w", err)
+	}
+
+	q := searchURL.Query()
+	q.Add("ts", strconv.FormatInt(time.Now().Unix(), 10))
+	searchURL.RawQuery = q.Encode()
+
+	// Sign the request using Ollama key (~/.ollama/id_ed25519)
+	// This authenticates with ollama.com using the local signing key
+	ctx := context.Background()
+	data := fmt.Appendf(nil, "%s,%s", http.MethodPost, searchURL.RequestURI())
+	signature, err := auth.Sign(ctx, data)
+	if err != nil {
+		return "", fmt.Errorf("signing request: %w", err)
+	}
+
+	req, err := http.NewRequestWithContext(ctx, http.MethodPost, searchURL.String(), bytes.NewBuffer(jsonBody))
 	if err != nil {
 		return "", fmt.Errorf("creating request: %w", err)
 	}
 
 	req.Header.Set("Content-Type", "application/json")
-	req.Header.Set("Authorization", "Bearer "+apiKey)
+	if signature != "" {
+		req.Header.Set("Authorization", fmt.Sprintf("Bearer %s", signature))
+	}
 
 	// Send request
 	client := &http.Client{Timeout: webSearchTimeout}
@@ -111,6 +135,9 @@ func (w *WebSearchTool) Execute(args map[string]any) (string, error) {
 		return "", fmt.Errorf("reading response: %w", err)
 	}
 
+	if resp.StatusCode == http.StatusUnauthorized {
+		return "", ErrWebSearchAuthRequired
+	}
 	if resp.StatusCode != http.StatusOK {
 		return "", fmt.Errorf("web search API returned status %d: %s", resp.StatusCode, string(body))
 	}
diff --git a/x/tools/websearch_test.go b/x/tools/websearch_test.go
new file mode 100644
index 000000000..8f5774728
--- /dev/null
+++ b/x/tools/websearch_test.go
@@ -0,0 +1,58 @@
+package tools
+
+import (
+	"errors"
+	"testing"
+)
+
+func TestWebSearchTool_Name(t *testing.T) {
+	tool := &WebSearchTool{}
+	if tool.Name() != "web_search" {
+		t.Errorf("expected name 'web_search', got '%s'", tool.Name())
+	}
+}
+
+func TestWebSearchTool_Description(t *testing.T) {
+	tool := &WebSearchTool{}
+	if tool.Description() == "" {
+		t.Error("expected non-empty description")
+	}
+}
+
+func TestWebSearchTool_Execute_MissingQuery(t *testing.T) {
+	tool := &WebSearchTool{}
+
+	// Test with no query
+	_, err := tool.Execute(map[string]any{})
+	if err == nil {
+		t.Error("expected error for missing query")
+	}
+
+	// Test with empty query
+	_, err = tool.Execute(map[string]any{"query": ""})
+	if err == nil {
+		t.Error("expected error for empty query")
+	}
+}
+
+func TestErrWebSearchAuthRequired(t *testing.T) {
+	// Test that the error type exists and can be checked with errors.Is
+	err := ErrWebSearchAuthRequired
+	if err == nil {
+		t.Fatal("ErrWebSearchAuthRequired should not be nil")
+	}
+
+	if err.Error() != "web search requires authentication" {
+		t.Errorf("unexpected error message: %s", err.Error())
+	}
+
+	// Test that errors.Is works
+	wrappedErr := errors.New("wrapped: " + err.Error())
+	if errors.Is(wrappedErr, ErrWebSearchAuthRequired) {
+		t.Error("wrapped error should not match with errors.Is")
+	}
+
+	if !errors.Is(ErrWebSearchAuthRequired, ErrWebSearchAuthRequired) {
+		t.Error("ErrWebSearchAuthRequired should match itself with errors.Is")
+	}
+}