@@ -4,6 +4,7 @@ import (
 	"encoding/json"
 	"fmt"
 	"os"
+	"sort"
 	"strings"
 
 	"github.com/pipeboard-co/pipeboard-cli/internal/client"
@@ -167,6 +168,28 @@ func runMCPToolsCall(cmd *cobra.Command, args []string) error {
 		return emitJSONError(fmt.Errorf("tool call failed: %w", err))
 	}
 
+	if isToolNotFound(result) {
+		if !mcpJSON {
+			fmt.Fprintf(os.Stderr, "Tool not found; refreshing tool list and retrying...\n")
+		}
+		tools, listErr := c.ListTools(mcpServer)
+		if listErr != nil {
+			return emitJSONError(fmt.Errorf("tool not found and tools/list failed: %w", listErr))
+		}
+		if toolExists(tools.Tools, mcpToolName) {
+			result, err = c.CallTool(mcpServer, mcpToolName, toolArgs)
+			if err != nil {
+				return emitJSONError(fmt.Errorf("tool call failed: %w", err))
+			}
+		} else {
+			msg := fmt.Sprintf("tool %q not found on server %q", mcpToolName, mcpServer)
+			if suggestions := similarTools(tools.Tools, mcpToolName, 5); len(suggestions) > 0 {
+				msg += " (did you mean: " + strings.Join(suggestions, ", ") + "?)"
+			}
+			return emitJSONError(fmt.Errorf("%s", msg))
+		}
+	}
+
 	if mcpJSON {
 		return emitToolResultJSON(result)
 	}
@@ -254,6 +277,69 @@ func emitToolResultJSON(raw json.RawMessage) error {
 	return emitJSON(out)
 }
 
+// isToolNotFound reports whether a tools/call result is an isError envelope
+// whose text begins with "Tool not found". That signal is what triggers an
+// implicit tools/list refresh and one retry.
+func isToolNotFound(raw json.RawMessage) bool {
+	var env struct {
+		Content []struct {
+			Text string `json:"text"`
+		} `json:"content"`
+		IsError bool `json:"isError"`
+	}
+	if err := json.Unmarshal(raw, &env); err != nil {
+		return false
+	}
+	if !env.IsError || len(env.Content) == 0 {
+		return false
+	}
+	return strings.HasPrefix(env.Content[0].Text, "Tool not found")
+}
+
+func toolExists(tools []client.ToolDefinition, name string) bool {
+	for _, t := range tools {
+		if t.Name == name {
+			return true
+		}
+	}
+	return false
+}
+
+// similarTools returns up to max tool names that share underscore-separated
+// tokens with name, ranked by shared-token count. Used to produce a
+// "did you mean" hint when a tool is genuinely missing.
+func similarTools(tools []client.ToolDefinition, name string, max int) []string {
+	tokens := strings.Split(strings.ToLower(name), "_")
+	type scored struct {
+		name  string
+		score int
+	}
+	var candidates []scored
+	for _, t := range tools {
+		lower := strings.ToLower(t.Name)
+		score := 0
+		for _, tok := range tokens {
+			if len(tok) > 1 && strings.Contains(lower, tok) {
+				score++
+			}
+		}
+		if score > 0 {
+			candidates = append(candidates, scored{t.Name, score})
+		}
+	}
+	sort.SliceStable(candidates, func(i, j int) bool {
+		return candidates[i].score > candidates[j].score
+	})
+	if len(candidates) > max {
+		candidates = candidates[:max]
+	}
+	out := make([]string, len(candidates))
+	for i, c := range candidates {
+		out[i] = c.name
+	}
+	return out
+}
+
 func truncate(s string, max int) string {
 	s = strings.ReplaceAll(s, "\n", " ")
 	if len(s) <= max {
 
@@ -5,6 +5,8 @@ import (
 	"io"
 	"os"
 	"testing"
+
+	"github.com/pipeboard-co/pipeboard-cli/internal/client"
 )
 
 // captureStdout runs fn with os.Stdout redirected to a pipe and returns the
@@ -125,6 +127,43 @@ func TestEmitToolResultJSON_PassthroughWhenNotEnvelope(t *testing.T) {
 	}
 }
 
+func TestIsToolNotFound(t *testing.T) {
+	tests := []struct {
+		name string
+		raw  string
+		want bool
+	}{
+		{"tool not found envelope", `{"content":[{"type":"text","text":"Tool not found: foo"}],"isError":true}`, true},
+		{"isError but different message", `{"content":[{"type":"text","text":"auth expired"}],"isError":true}`, false},
+		{"not an error", `{"content":[{"type":"text","text":"Tool not found: foo"}],"isError":false}`, false},
+		{"no content", `{"content":[],"isError":true}`, false},
+		{"garbage", `not json`, false},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := isToolNotFound(json.RawMessage(tt.raw)); got != tt.want {
+				t.Errorf("isToolNotFound = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}
+
+func TestSimilarTools(t *testing.T) {
+	tools := []client.ToolDefinition{
+		{Name: "list_snap_audiences"},
+		{Name: "list_snap_campaigns"},
+		{Name: "list_meta_campaigns"},
+		{Name: "get_snap_segment_details"},
+	}
+	got := similarTools(tools, "list_snap_segments", 3)
+	if len(got) == 0 {
+		t.Fatalf("expected suggestions, got none")
+	}
+	if got[0] != "list_snap_audiences" && got[0] != "list_snap_campaigns" {
+		t.Errorf("top suggestion should be a list_snap_* tool, got %q", got[0])
+	}
+}
+
 func TestEmitJSONError_InJSONMode(t *testing.T) {
 	prev := mcpJSON
 	mcpJSON = true