diff --git a/src/fabledassistant/services/generation_task.py b/src/fabledassistant/services/generation_task.py
index d3e90dd..6808101 100644
--- a/src/fabledassistant/services/generation_task.py
+++ b/src/fabledassistant/services/generation_task.py
@@ -410,18 +410,20 @@ async def run_generation(
             buf.append_event("status", {"status": "Generating response..." if _round == 0 else "Composing response..."})
             t_stream = time.monotonic()
 
-            round_content_start = len(buf.content_so_far)
-            round_tokens_start = timing.get("output_tokens") or 0
-            round_prompt_tokens_start = timing.get("prompt_tokens") or 0
             approx_msg_chars = sum(len(str(m.get("content", ""))) for m in messages)
             effective_think = think
             retried_with_think = False
-            logger.info(
-                "CTX_DIAG round_start conv=%d round=%d num_ctx=%d msgs=%d approx_chars=%d think=%s",
-                conv_id, _round, num_ctx, len(messages), approx_msg_chars, effective_think,
-            )
+            attempt = 0
 
             while True:
+                attempt_content_start = len(buf.content_so_far)
+                attempt_output_tokens_start = timing.get("output_tokens") or 0
+                attempt_prompt_tokens_start = timing.get("prompt_tokens") or 0
+                attempt_tool_calls_start = len(round_tool_calls)
+                logger.info(
+                    "CTX_DIAG attempt_start conv=%d round=%d attempt=%d num_ctx=%d msgs=%d approx_chars=%d think=%s",
+                    conv_id, _round, attempt, num_ctx, len(messages), approx_msg_chars, effective_think,
+                )
                 async for chunk in _stream_with_retry(messages, model, tools, effective_think, num_ctx=num_ctx):
                     if buf.cancel_event.is_set():
                         cancelled = True
@@ -523,24 +525,23 @@ async def run_generation(
                 if cancelled:
                     break
 
-                round_content_added = len(buf.content_so_far) - round_content_start
-                round_tokens_added = (timing.get("output_tokens") or 0) - round_tokens_start
-                round_prompt_tokens = (timing.get("prompt_tokens") or 0) - round_prompt_tokens_start
-                headroom = num_ctx - round_prompt_tokens if round_prompt_tokens else None
+                attempt_content_added = len(buf.content_so_far) - attempt_content_start
+                attempt_tokens_added = (timing.get("output_tokens") or 0) - attempt_output_tokens_start
+                attempt_prompt_tokens = (timing.get("prompt_tokens") or 0) - attempt_prompt_tokens_start
+                attempt_tool_calls_added = len(round_tool_calls) - attempt_tool_calls_start
+                headroom = num_ctx - attempt_prompt_tokens if attempt_prompt_tokens else None
                 is_silent = (
-                    not round_tool_calls
-                    and round_content_added == 0
-                    and round_tokens_added > 0
+                    attempt_tool_calls_added == 0
+                    and attempt_content_added == 0
+                    and attempt_tokens_added > 0
                 )
                 logger.info(
-                    "CTX_DIAG round_end conv=%d round=%d think=%s prompt_tokens=%d output_tokens=%d headroom=%s content_added=%d tool_calls=%d silent=%s",
-                    conv_id, _round, effective_think, round_prompt_tokens, round_tokens_added,
-                    headroom, round_content_added, len(round_tool_calls), is_silent,
+                    "CTX_DIAG attempt_end conv=%d round=%d attempt=%d think=%s prompt_tokens=%d output_tokens=%d headroom=%s content_added=%d tool_calls=%d silent=%s",
+                    conv_id, _round, attempt, effective_think, attempt_prompt_tokens, attempt_tokens_added,
+                    headroom, attempt_content_added, attempt_tool_calls_added, is_silent,
                 )
                 if (
-                    not round_tool_calls
-                    and round_content_added == 0
-                    and round_tokens_added > 0
+                    is_silent
                     and not effective_think
                     and not retried_with_think
                 ):
@@ -549,11 +550,12 @@ async def run_generation(
                     # think=True — reasoning mode produces more reliable output.
                     logger.warning(
                         "Silent round %d for conv %d (tokens=%d); retrying with think=True",
-                        _round, conv_id, round_tokens_added,
+                        _round, conv_id, attempt_tokens_added,
                     )
                     buf.append_event("status", {"status": "Retrying with reasoning enabled..."})
                     effective_think = True
                     retried_with_think = True
+                    attempt += 1
                     continue
                 break