Fix Strands SDK tool pairing, CCR marker format, and startup timeout (#114 #116 #117)

- Increase headroom wrap startup timeout from 15s to 45s (#114)
  ML components (Kompress, Magika, Tree-sitter) need 20-30s on slower machines

- Detect Strands SDK toolUse/toolResult blocks in find_tool_units (#116)
  Strands wraps tools as {"toolUse": {"toolUseId": ...}} not {"type": "tool_use"}
  Without this, tool pairs aren't grouped and dropping one breaks Anthropic validation

- Match CCR marker content format to conversation style (#117)
  Strands expects list-of-blocks content, not plain strings
  Detect format from existing messages and match it

headroom/cli/wrap.py

@@ -108,8 +108,10 @@ def _start_proxy(
         env=proxy_env,
     )
 
-    # Wait for proxy to be ready (up to 15 seconds)
-    for _i in range(15):
+    # Wait for proxy to be ready (up to 45 seconds).
+    # ML components (Kompress, Magika, Tree-sitter) load synchronously before
+    # uvicorn binds the port. On slower machines this can take 20-30 seconds.
+    for _i in range(45):
         time.sleep(1)
         if _check_proxy(port):
             click.echo(f"  Logs: {log_path}")
@@ -126,7 +128,7 @@ def _start_proxy(
 
     proc.kill()
     log_file.close()
-    raise RuntimeError(f"Proxy failed to start on port {port} within 15 seconds")
+    raise RuntimeError(f"Proxy failed to start on port {port} within 45 seconds")
 
 
 def _setup_rtk(verbose: bool = False) -> Path | None:

headroom/parser.py

@@ -267,14 +267,21 @@ def find_tool_units(messages: list[dict[str, Any]]) -> list[tuple[int, list[int]
                 tool_response_map[tc_id] = i
 
         # Anthropic format: role="user" with content blocks containing tool_result
+        # Also handles Strands SDK format: {"toolResult": {"toolUseId": "..."}}
         if msg.get("role") == "user":
             content = msg.get("content")
             if isinstance(content, list):
                 for block in content:
-                    if isinstance(block, dict) and block.get("type") == "tool_result":
-                        tc_id = block.get("tool_use_id")
-                        if tc_id:
-                            tool_response_map[tc_id] = i
+                    if isinstance(block, dict):
+                        if block.get("type") == "tool_result":
+                            tc_id = block.get("tool_use_id")
+                            if tc_id:
+                                tool_response_map[tc_id] = i
+                        elif "toolResult" in block:
+                            # Strands SDK format
+                            tc_id = block["toolResult"].get("toolUseId")
+                            if tc_id:
+                                tool_response_map[tc_id] = i
 
     # Find assistant messages with tool calls
     for i, msg in enumerate(messages):
@@ -292,13 +299,20 @@ def find_tool_units(messages: list[dict[str, Any]]) -> list[tuple[int, list[int]
                     response_indices.append(tool_response_map[tc_id])
 
         # Anthropic format: content blocks with type=tool_use
+        # Also handles Strands SDK format: {"toolUse": {"toolUseId": "..."}}
         content = msg.get("content")
         if isinstance(content, list):
             for block in content:
-                if isinstance(block, dict) and block.get("type") == "tool_use":
-                    tc_id = block.get("id")
-                    if tc_id and tc_id in tool_response_map:
-                        response_indices.append(tool_response_map[tc_id])
+                if isinstance(block, dict):
+                    if block.get("type") == "tool_use":
+                        tc_id = block.get("id")
+                        if tc_id and tc_id in tool_response_map:
+                            response_indices.append(tool_response_map[tc_id])
+                    elif "toolUse" in block:
+                        # Strands SDK format
+                        tc_id = block["toolUse"].get("toolUseId")
+                        if tc_id and tc_id in tool_response_map:
+                            response_indices.append(tool_response_map[tc_id])
 
         if response_indices:
             # Use set to deduplicate in case same message has both formats

headroom/transforms/intelligent_context.py

@@ -449,9 +449,21 @@ class IntelligentContextManager(Transform):
             else:
                 insert_idx = len(result_messages)
 
+            # Match the content format of existing messages.
+            # Strands SDK uses list-of-blocks: [{"text": "..."}]
+            # Anthropic/OpenAI use plain strings.
+            # Check what format the conversation uses and match it.
+            _uses_block_format = any(
+                isinstance(m.get("content"), list)
+                for m in result_messages
+                if m.get("role") == "user"
+            )
+            marker_content: str | list[dict[str, str]] = (
+                [{"type": "text", "text": marker}] if _uses_block_format else marker
+            )
             result_messages.insert(
                 insert_idx,
-                {"role": "user", "content": marker},
+                {"role": "user", "content": marker_content},
             )
 
             transforms_applied.append(f"intelligent_cap:{dropped_count}")

headroom/transforms/rolling_window.py

@@ -175,11 +175,20 @@ class RollingWindow(Transform):
             else:
                 insert_idx = len(result_messages)
 
+            # Match content format (Strands uses list-of-blocks, Anthropic uses string)
+            _uses_block_format = any(
+                isinstance(m.get("content"), list)
+                for m in result_messages
+                if m.get("role") == "user"
+            )
+            marker_content: str | list[dict[str, str]] = (
+                [{"type": "text", "text": marker}] if _uses_block_format else marker
+            )
             result_messages.insert(
                 insert_idx,
                 {
                     "role": "user",
-                    "content": marker,
+                    "content": marker_content,
                 },
             )