diff --git a/pkg/agent/loop.go b/pkg/agent/loop.go
index 3469d00..9ebe9be 100644
--- a/pkg/agent/loop.go
+++ b/pkg/agent/loop.go
@@ -179,6 +179,17 @@ func run(ctx context.Context, cfg agentConfig, state state) error {
 			return fmt.Errorf("step %d: %s", step, stopReason)
 		}
 
+		// Detect models that emit tool calls as plain text instead of using the
+		// function-calling API. If the response contains no API-level tool calls
+		// but the text matches a registered tool name followed by ':' or '(',
+		// the model does not support function calling — treat as ToolUnsupportedError
+		// so freeloader can blacklist and cycle to the next model.
+		if len(toolCalls) == 0 && len(cfg.Tools) > 0 && hasTextToolCall(content.String(), cfg.Tools) {
+			return fmt.Errorf("step %d: %w", step, &backend.ToolUnsupportedError{
+				Message: "model emitted tool call as text (function calling API not supported)",
+			})
+		}
+
 		// Execute tool calls, running consecutive parallel-read-safe tools concurrently.
 		msg := backend.Message{Role: "assistant", Content: content.String(), ToolCalls: toolCalls}
 		results := make([]toolResult, 0, len(toolCalls))
@@ -369,6 +380,18 @@ func emit(cfg agentConfig, msg Event) {
 	}
 }
 
+// hasTextToolCall returns true when the assistant text contains a registered
+// tool name immediately followed by ':' or '(', indicating the model tried to
+// invoke a tool by writing the call as plain text rather than via the API.
+func hasTextToolCall(text string, tools []backend.Tool) bool {
+	for _, t := range tools {
+		if strings.Contains(text, t.Name+":") || strings.Contains(text, t.Name+"(") {
+			return true
+		}
+	}
+	return false
+}
+
 // classifyError returns a short string identifying the error type for the
 // turnError hook payload.
 func classifyError(err error) string {
diff --git a/pkg/agent/loop_texttool_test.go b/pkg/agent/loop_texttool_test.go
new file mode 100644
index 0000000..9c9dda5
--- /dev/null
+++ b/pkg/agent/loop_texttool_test.go
@@ -0,0 +1,76 @@
+package agent
+
+import (
+	"context"
+	"testing"
+
+	"ollie/pkg/backend"
+)
+
+// TestTextToolCall_DetectedAsUnsupported verifies that when a model emits a tool
+// call as plain text (no API-level tool calls) the loop returns a
+// ToolUnsupportedError so freeloader can blacklist and cycle.
+func TestTextToolCall_DetectedAsUnsupported(t *testing.T) {
+	be := defaultBE()
+	// Model responds with text that mimics a tool invocation instead of using
+	// the function-calling API.
+	be.respond = func(_ context.Context, _ []backend.Message, _ []backend.Tool, _ backend.GenerationParams) (<-chan backend.StreamEvent, error) {
+		return textStream(`execute_code: steps=[{code: "print('hi')"}]`), nil
+	}
+
+	c := newCore(t, be, nil)
+	c.cfg.Tools = []backend.Tool{{Name: "execute_code", Description: "run code"}}
+
+	evs := collectEvents(context.Background(), c, "run something")
+
+	errEvs := byRole(evs, "error")
+	if len(errEvs) == 0 {
+		t.Fatal("expected an error event; got none")
+	}
+	// The error must mention tool_unsupported behaviour (not a plain backend error).
+	if got := errEvs[0]; got == "" {
+		t.Error("error event content is empty")
+	}
+}
+
+// TestTextToolCall_NoFalsePositive verifies that a normal text response that
+// does not contain a tool-call pattern is not mistakenly flagged.
+func TestTextToolCall_NoFalsePositive(t *testing.T) {
+	be := defaultBE()
+	be.respond = func(_ context.Context, _ []backend.Message, _ []backend.Tool, _ backend.GenerationParams) (<-chan backend.StreamEvent, error) {
+		return textStream("Here is how execute_code works in general."), nil
+	}
+
+	c := newCore(t, be, nil)
+	c.cfg.Tools = []backend.Tool{{Name: "execute_code", Description: "run code"}}
+
+	evs := collectEvents(context.Background(), c, "explain tools")
+
+	errEvs := byRole(evs, "error")
+	if len(errEvs) != 0 {
+		t.Errorf("unexpected error events: %v", errEvs)
+	}
+	assistEvs := byRole(evs, "assistant")
+	if len(assistEvs) == 0 {
+		t.Error("expected assistant response; got none")
+	}
+}
+
+// TestTextToolCall_NoToolsConfigured verifies that when no tools are configured
+// the detection does not fire (nothing to detect against).
+func TestTextToolCall_NoToolsConfigured(t *testing.T) {
+	be := defaultBE()
+	be.respond = func(_ context.Context, _ []backend.Message, _ []backend.Tool, _ backend.GenerationParams) (<-chan backend.StreamEvent, error) {
+		return textStream(`execute_code: steps=[{code: "print('hi')"}]`), nil
+	}
+
+	c := newCore(t, be, nil)
+	// No tools configured.
+
+	evs := collectEvents(context.Background(), c, "run something")
+
+	errEvs := byRole(evs, "error")
+	if len(errEvs) != 0 {
+		t.Errorf("unexpected error with no tools configured: %v", errEvs)
+	}
+}