diff --git a/fern/openapi.json b/fern/openapi.json
index 2647f06e..eb428df1 100644
--- a/fern/openapi.json
+++ b/fern/openapi.json
@@ -30242,6 +30242,60 @@
             "title": "Core Memory",
             "description": "The content of the core memory."
           },
+          "num_tokens_memory_filesystem": {
+            "type": "integer",
+            "title": "Num Tokens Memory Filesystem",
+            "description": "The number of tokens in the memory filesystem section (git-enabled agents only).",
+            "default": 0
+          },
+          "memory_filesystem": {
+            "anyOf": [
+              {
+                "type": "string"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Memory Filesystem",
+            "description": "The content of the memory filesystem section."
+          },
+          "num_tokens_tool_usage_rules": {
+            "type": "integer",
+            "title": "Num Tokens Tool Usage Rules",
+            "description": "The number of tokens in the tool usage rules section.",
+            "default": 0
+          },
+          "tool_usage_rules": {
+            "anyOf": [
+              {
+                "type": "string"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Tool Usage Rules",
+            "description": "The content of the tool usage rules section."
+          },
+          "num_tokens_directories": {
+            "type": "integer",
+            "title": "Num Tokens Directories",
+            "description": "The number of tokens in the directories section (attached sources).",
+            "default": 0
+          },
+          "directories": {
+            "anyOf": [
+              {
+                "type": "string"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Directories",
+            "description": "The content of the directories section."
+          },
           "num_tokens_summary_memory": {
             "type": "integer",
             "title": "Num Tokens Summary Memory",
diff --git a/letta/agents/base_agent.py b/letta/agents/base_agent.py
index e072146d..94d18232 100644
--- a/letta/agents/base_agent.py
+++ b/letta/agents/base_agent.py
@@ -125,6 +125,9 @@ class BaseAgent(ABC):
 
             # extract the dynamic section that includes memory blocks, tool rules, and directories
             # this avoids timestamp comparison issues
+            # TODO: This is a separate position-based parser for the same system message format
+            # parsed by ContextWindowCalculator.extract_system_components(). Consider unifying
+            # to avoid divergence. See PR #9398 for context.
             def extract_dynamic_section(text):
                 start_marker = "</base_instructions>"
                 end_marker = "<memory_metadata>"
diff --git a/letta/schemas/memory.py b/letta/schemas/memory.py
index 496eb308..b4ca07cf 100644
--- a/letta/schemas/memory.py
+++ b/letta/schemas/memory.py
@@ -43,6 +43,17 @@ class ContextWindowOverview(BaseModel):
     num_tokens_core_memory: int = Field(..., description="The number of tokens in the core memory.")
     core_memory: str = Field(..., description="The content of the core memory.")
 
+    num_tokens_memory_filesystem: int = Field(
+        0, description="The number of tokens in the memory filesystem section (git-enabled agents only)."
+    )
+    memory_filesystem: Optional[str] = Field(None, description="The content of the memory filesystem section.")
+
+    num_tokens_tool_usage_rules: int = Field(0, description="The number of tokens in the tool usage rules section.")
+    tool_usage_rules: Optional[str] = Field(None, description="The content of the tool usage rules section.")
+
+    num_tokens_directories: int = Field(0, description="The number of tokens in the directories section (attached sources).")
+    directories: Optional[str] = Field(None, description="The content of the directories section.")
+
     num_tokens_summary_memory: int = Field(..., description="The number of tokens in the summary memory.")
     summary_memory: Optional[str] = Field(None, description="The content of the summary memory.")
 
diff --git a/letta/services/context_window_calculator/context_window_calculator.py b/letta/services/context_window_calculator/context_window_calculator.py
index b228b532..f4ad2e07 100644
--- a/letta/services/context_window_calculator/context_window_calculator.py
+++ b/letta/services/context_window_calculator/context_window_calculator.py
@@ -1,5 +1,5 @@
 import asyncio
-from typing import Any, List, Optional, Tuple
+from typing import Any, Dict, List, Optional, Tuple
 
 from openai.types.beta.function_tool import FunctionTool as OpenAITool
 
@@ -20,68 +20,195 @@ class ContextWindowCalculator:
     """Handles context window calculations with different token counting strategies"""
 
     @staticmethod
-    def extract_system_components(system_message: str) -> Tuple[str, str, str]:
-        """Extract system prompt + core memory + metadata from a system message.
-
-        Historically, Letta system messages were formatted with:
-        - <base_instructions> ...
-        - <memory_blocks> ...
-        - <memory_metadata> ...
-
-        Git-backed memory agents do NOT wrap their rendered memory in <memory_blocks>.
-        Instead, the memory content typically begins with <memory_filesystem> followed
-        by file-like tags such as <system/human.md>...</system/human.md>.
-        
-        This helper supports both formats so the context window preview can display
-        core memory for git-enabled agents.
+    def _extract_tag_content(text: str, tag_name: str) -> Optional[str]:
         """
+        Extract content between XML-style opening and closing tags.
 
-        base_start = system_message.find("<base_instructions>")
-        memory_blocks_start = system_message.find("<memory_blocks>")
-        if memory_blocks_start == -1:
-            # Git-memory-enabled agents render <memory_filesystem> instead of <memory_blocks>
-            memory_blocks_start = system_message.find("<memory_filesystem>")
-        metadata_start = system_message.find("<memory_metadata>")
+        Args:
+            text: The text to search in
+            tag_name: The name of the tag (without < >)
 
-        system_prompt = ""
-        core_memory = ""
-        external_memory_summary = ""
+        Returns:
+            The content between tags (inclusive of tags), or None if not found
 
-        # Always extract metadata if present
-        if metadata_start != -1:
-            external_memory_summary = system_message[metadata_start:].strip()
+        Note:
+            If duplicate tags exist, only the first occurrence is extracted.
+        """
+        start_tag = f"<{tag_name}>"
+        end_tag = f"</{tag_name}>"
 
-        # Preferred (legacy) parsing when tags are present
-        if base_start != -1 and memory_blocks_start != -1:
-            system_prompt = system_message[base_start:memory_blocks_start].strip()
-        if memory_blocks_start != -1 and metadata_start != -1:
-            core_memory = system_message[memory_blocks_start:metadata_start].strip()
+        start_idx = text.find(start_tag)
+        if start_idx == -1:
+            return None
 
-        # Fallback parsing for git-backed memory rendering (no <memory_blocks> wrapper)
-        if not core_memory and metadata_start != -1:
-            # Identify where the "memory" section begins.
-            candidates = []
-            for marker in (
-                "<memory_filesystem>",
-                "<system/",  # e.g. <system/human.md>
-                "<organization/",  # future-proofing
-            ):
-                pos = system_message.find(marker)
-                if pos != -1:
-                    candidates.append(pos)
+        end_idx = text.find(end_tag, start_idx)
+        if end_idx == -1:
+            return None
 
-            # If <memory_blocks> is present but core_memory wasn't extracted (e.g. missing base tags),
-            # allow it as a candidate as well.
-            if memory_blocks_start != -1:
-                candidates.append(memory_blocks_start)
+        return text[start_idx : end_idx + len(end_tag)]
 
-            if candidates:
-                mem_start = min(candidates)
-                core_memory = system_message[mem_start:metadata_start].strip()
-                if not system_prompt:
-                    system_prompt = system_message[:mem_start].strip()
+    @staticmethod
+    def _extract_system_prompt(system_message: str) -> Optional[str]:
+        """
+        Extract the system prompt / base instructions from a system message.
 
-        return system_prompt, core_memory, external_memory_summary
+        First tries to find an explicit <base_instructions> tag. If not present
+        (e.g. custom system prompts from Letta Code agents), falls back to
+        extracting everything before the first known section tag.
+
+        Returns:
+            The system prompt text, or None if the message is empty.
+
+        Note:
+            The returned value is semantically different depending on agent type:
+            - Standard agents: includes the <base_instructions>...</base_instructions> tags
+            - Custom prompt agents (e.g. Letta Code): raw preamble text without any tags
+        """
+        _extract = ContextWindowCalculator._extract_tag_content
+
+        # Preferred: explicit <base_instructions> wrapper
+        tagged = _extract(system_message, "base_instructions")
+        if tagged is not None:
+            return tagged
+
+        # Fallback: everything before the first known section tag
+        section_tags = ["<memory_blocks>", "<memory_filesystem>", "<tool_usage_rules>", "<directories>", "<memory_metadata>"]
+        first_section_pos = len(system_message)
+        for tag in section_tags:
+            pos = system_message.find(tag)
+            if pos != -1 and pos < first_section_pos:
+                first_section_pos = pos
+
+        prompt = system_message[:first_section_pos].strip()
+        return prompt if prompt else None
+
+    @staticmethod
+    def _extract_top_level_tag(system_message: str, tag_name: str, container_tag: str = "memory_blocks") -> Optional[str]:
+        """
+        Extract a tag only if it appears outside a container tag.
+
+        This prevents extracting tags that are nested inside <memory_blocks> as
+        memory block labels (e.g. a block named "memory_filesystem" rendered as
+        <memory_filesystem> inside <memory_blocks>) from being confused with
+        top-level sections.
+
+        Handles the case where a tag appears both nested (inside the container)
+        and at top-level — scans all occurrences to find one outside the container.
+
+        Args:
+            system_message: The full system message text
+            tag_name: The tag to extract
+            container_tag: The container tag to check nesting against
+
+        Returns:
+            The tag content if found at top level, None otherwise.
+        """
+        _extract = ContextWindowCalculator._extract_tag_content
+
+        start_tag = f"<{tag_name}>"
+        end_tag = f"</{tag_name}>"
+
+        # Find the container boundaries
+        container_start = system_message.find(f"<{container_tag}>")
+        container_end = system_message.find(f"</{container_tag}>")
+        has_container = container_start != -1 and container_end != -1
+
+        # Scan all occurrences of the tag to find one outside the container
+        search_start = 0
+        while True:
+            tag_start = system_message.find(start_tag, search_start)
+            if tag_start == -1:
+                return None
+
+            # Check if this occurrence is nested inside the container
+            if has_container and container_start < tag_start < container_end:
+                # Skip past this nested occurrence
+                search_start = tag_start + len(start_tag)
+                continue
+
+            # Found a top-level occurrence — extract it
+            tag_end = system_message.find(end_tag, tag_start)
+            if tag_end == -1:
+                return None
+            return system_message[tag_start : tag_end + len(end_tag)]
+
+    @staticmethod
+    def _extract_git_core_memory(system_message: str) -> Optional[str]:
+        """
+        Extract bare file blocks for git-enabled agents.
+
+        Git-enabled agents render individual memory blocks as bare tags like
+        <system/human.md>...</system/human.md> WITHOUT any container tag.
+        These appear after </memory_filesystem> and before the next known
+        section tag (<tool_usage_rules>, <directories>, or <memory_metadata>).
+
+        Returns:
+            The text containing all bare file blocks, or None if not found.
+        """
+        end_marker = "</memory_filesystem>"
+        end_pos = system_message.find(end_marker)
+        if end_pos == -1:
+            return None
+
+        start = end_pos + len(end_marker)
+
+        # Find the next known section tag
+        next_section_tags = ["<tool_usage_rules>", "<directories>", "<memory_metadata>"]
+        next_section_pos = len(system_message)
+        for tag in next_section_tags:
+            pos = system_message.find(tag, start)
+            if pos != -1 and pos < next_section_pos:
+                next_section_pos = pos
+
+        content = system_message[start:next_section_pos].strip()
+        return content if content else None
+
+    @staticmethod
+    def extract_system_components(system_message: str) -> Dict[str, Optional[str]]:
+        """
+        Extract structured components from a formatted system message.
+
+        Parses the system message to extract sections marked by XML-style tags using
+        proper end-tag matching. Handles all agent types including:
+        - Standard agents with <base_instructions> wrapper
+        - Custom system prompts without <base_instructions> (e.g. Letta Code agents)
+        - Git-enabled agents with top-level <memory_filesystem> and bare file blocks
+        - React/workflow agents that don't render <memory_blocks>
+
+        Args:
+            system_message: A formatted system message containing XML-style section markers
+
+        Returns:
+            A dictionary with the following keys (value is None if section not found):
+            - system_prompt: The base instructions section (or text before first section tag)
+            - core_memory: The memory blocks section. For standard agents this is the
+              <memory_blocks>...</memory_blocks> content. For git-enabled agents (no
+              <memory_blocks> but top-level <memory_filesystem>), this captures the bare
+              file blocks (e.g. <system/human.md>) that follow </memory_filesystem>.
+            - memory_filesystem: Top-level memory filesystem (git-enabled agents only, NOT
+              the memory_filesystem block nested inside <memory_blocks>)
+            - tool_usage_rules: The tool usage rules section
+            - directories: The directories section (when sources are attached)
+            - external_memory_summary: The memory metadata section
+        """
+        _extract = ContextWindowCalculator._extract_tag_content
+        _extract_top = ContextWindowCalculator._extract_top_level_tag
+
+        core_memory = _extract(system_message, "memory_blocks")
+        memory_filesystem = _extract_top(system_message, "memory_filesystem")
+
+        # Git-enabled agents: no <memory_blocks>, but bare file blocks after </memory_filesystem>
+        if core_memory is None and memory_filesystem is not None:
+            core_memory = ContextWindowCalculator._extract_git_core_memory(system_message)
+
+        return {
+            "system_prompt": ContextWindowCalculator._extract_system_prompt(system_message),
+            "core_memory": core_memory,
+            "memory_filesystem": memory_filesystem,
+            "tool_usage_rules": _extract_top(system_message, "tool_usage_rules"),
+            "directories": _extract_top(system_message, "directories"),
+            "external_memory_summary": _extract(system_message, "memory_metadata"),
+        }
 
     @staticmethod
     def extract_summary_memory(messages: List[Any]) -> Tuple[Optional[str], int]:
@@ -154,9 +281,14 @@ class ContextWindowCalculator:
         converted_messages = token_counter.convert_messages(in_context_messages)
 
         # Extract system components
-        system_prompt = ""
-        core_memory = ""
-        external_memory_summary = ""
+        components: Dict[str, Optional[str]] = {
+            "system_prompt": None,
+            "core_memory": None,
+            "memory_filesystem": None,
+            "tool_usage_rules": None,
+            "directories": None,
+            "external_memory_summary": None,
+        }
 
         if (
             in_context_messages
@@ -166,10 +298,15 @@ class ContextWindowCalculator:
             and isinstance(in_context_messages[0].content[0], TextContent)
         ):
             system_message = in_context_messages[0].content[0].text
-            system_prompt, core_memory, external_memory_summary = self.extract_system_components(system_message)
+            components = self.extract_system_components(system_message)
 
-        # System prompt
-        system_prompt = system_prompt or agent_state.system
+        # Extract each component with fallbacks
+        system_prompt = components.get("system_prompt") or agent_state.system or ""
+        core_memory = components.get("core_memory") or ""
+        memory_filesystem = components.get("memory_filesystem") or ""
+        tool_usage_rules = components.get("tool_usage_rules") or ""
+        directories = components.get("directories") or ""
+        external_memory_summary = components.get("external_memory_summary") or ""
 
         # Extract summary memory
         summary_memory, message_start_index = self.extract_summary_memory(in_context_messages)
@@ -179,11 +316,14 @@ class ContextWindowCalculator:
         if agent_state.tools:
             available_functions_definitions = [OpenAITool(type="function", function=f.json_schema) for f in agent_state.tools]
 
-        # Count tokens concurrently
+        # Count tokens concurrently for all sections, skipping empty ones
         token_counts = await asyncio.gather(
             token_counter.count_text_tokens(system_prompt),
-            token_counter.count_text_tokens(core_memory),
-            token_counter.count_text_tokens(external_memory_summary),
+            token_counter.count_text_tokens(core_memory) if core_memory else asyncio.sleep(0, result=0),
+            token_counter.count_text_tokens(memory_filesystem) if memory_filesystem else asyncio.sleep(0, result=0),
+            token_counter.count_text_tokens(tool_usage_rules) if tool_usage_rules else asyncio.sleep(0, result=0),
+            token_counter.count_text_tokens(directories) if directories else asyncio.sleep(0, result=0),
+            token_counter.count_text_tokens(external_memory_summary) if external_memory_summary else asyncio.sleep(0, result=0),
             token_counter.count_text_tokens(summary_memory) if summary_memory else asyncio.sleep(0, result=0),
             (
                 token_counter.count_message_tokens(converted_messages[message_start_index:])
@@ -200,6 +340,9 @@ class ContextWindowCalculator:
         (
             num_tokens_system,
             num_tokens_core_memory,
+            num_tokens_memory_filesystem,
+            num_tokens_tool_usage_rules,
+            num_tokens_directories,
             num_tokens_external_memory_summary,
             num_tokens_summary_memory,
             num_tokens_messages,
@@ -223,6 +366,14 @@ class ContextWindowCalculator:
             system_prompt=system_prompt,
             num_tokens_core_memory=num_tokens_core_memory,
             core_memory=core_memory,
+            # New sections
+            num_tokens_memory_filesystem=num_tokens_memory_filesystem,
+            memory_filesystem=memory_filesystem if memory_filesystem else None,
+            num_tokens_tool_usage_rules=num_tokens_tool_usage_rules,
+            tool_usage_rules=tool_usage_rules if tool_usage_rules else None,
+            num_tokens_directories=num_tokens_directories,
+            directories=directories if directories else None,
+            # Summary and messages
             num_tokens_summary_memory=num_tokens_summary_memory,
             summary_memory=summary_memory,
             num_tokens_messages=num_tokens_messages,
diff --git a/tests/helpers/utils.py b/tests/helpers/utils.py
index 52b13bc7..17715b91 100644
--- a/tests/helpers/utils.py
+++ b/tests/helpers/utils.py
@@ -186,6 +186,9 @@ def validate_context_window_overview(
     # 2. All token counts should be non-negative
     assert overview.num_tokens_system >= 0, "System token count cannot be negative"
     assert overview.num_tokens_core_memory >= 0, "Core memory token count cannot be negative"
+    assert overview.num_tokens_memory_filesystem >= 0, "Memory filesystem token count cannot be negative"
+    assert overview.num_tokens_tool_usage_rules >= 0, "Tool usage rules token count cannot be negative"
+    assert overview.num_tokens_directories >= 0, "Directories token count cannot be negative"
     assert overview.num_tokens_external_memory_summary >= 0, "External memory summary token count cannot be negative"
     assert overview.num_tokens_summary_memory >= 0, "Summary memory token count cannot be negative"
     assert overview.num_tokens_messages >= 0, "Messages token count cannot be negative"
@@ -195,6 +198,9 @@ def validate_context_window_overview(
     expected_total = (
         overview.num_tokens_system
         + overview.num_tokens_core_memory
+        + overview.num_tokens_memory_filesystem
+        + overview.num_tokens_tool_usage_rules
+        + overview.num_tokens_directories
         + overview.num_tokens_external_memory_summary
         + overview.num_tokens_summary_memory
         + overview.num_tokens_messages
@@ -244,13 +250,14 @@ def validate_context_window_overview(
     avg_tokens_per_message = overview.num_tokens_messages / overview.num_messages
     assert avg_tokens_per_message >= 0, "Average tokens per message should be non-negative"
 
-    # 16. Check attached file is visible
+    # 16. Check attached file is visible in the directories section
     if attached_file:
-        assert attached_file.visible_content in overview.core_memory, "File must be attached in core memory"
-        assert '<file status="open"' in overview.core_memory
-        assert "</file>" in overview.core_memory
-        assert "max_files_open" in overview.core_memory, "Max files should be set in core memory"
-        assert "current_files_open" in overview.core_memory, "Current files should be set in core memory"
+        assert overview.directories is not None, "Directories section must exist when files are attached"
+        assert attached_file.visible_content in overview.directories, "File must be attached in directories"
+        assert '<file status="open"' in overview.directories
+        assert "</file>" in overview.directories
+        assert "max_files_open" in overview.directories, "Max files should be set in directories"
+        assert "current_files_open" in overview.directories, "Current files should be set in directories"
 
     # Check for tools
     assert overview.num_tokens_functions_definitions > 0
diff --git a/tests/test_context_window_calculator.py b/tests/test_context_window_calculator.py
index de17a685..0f3f3035 100644
--- a/tests/test_context_window_calculator.py
+++ b/tests/test_context_window_calculator.py
@@ -1,17 +1,400 @@
+from unittest.mock import AsyncMock, MagicMock
+
 import pytest
 
 from letta.services.context_window_calculator.context_window_calculator import ContextWindowCalculator
 
 
-def test_extract_system_components_git_backed_memory_without_memory_blocks_wrapper():
-    system_message = """You are some system prompt.
+class TestExtractTagContent:
+    """Tests for the _extract_tag_content helper method"""
+
+    def test_extracts_simple_tag(self):
+        text = "prefix <tag>content</tag> suffix"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result == "<tag>content</tag>"
+
+    def test_returns_none_for_missing_tag(self):
+        text = "no tags here"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result is None
+
+    def test_returns_none_for_missing_opening_tag(self):
+        text = "content</tag>"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result is None
+
+    def test_returns_none_for_unclosed_tag(self):
+        text = "<tag>content without closing"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result is None
+
+    def test_handles_multiline_content(self):
+        text = "<tag>\nline1\nline2\n</tag>"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result == "<tag>\nline1\nline2\n</tag>"
+
+    def test_handles_nested_content(self):
+        text = "<outer><inner>nested</inner></outer>"
+        result = ContextWindowCalculator._extract_tag_content(text, "outer")
+        assert result == "<outer><inner>nested</inner></outer>"
+
+    def test_handles_empty_content(self):
+        text = "<tag></tag>"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result == "<tag></tag>"
+
+    def test_extracts_first_occurrence_with_duplicate_tags(self):
+        """When duplicate tags exist, only the first occurrence is extracted"""
+        text = "<tag>first</tag> some text <tag>second</tag>"
+        result = ContextWindowCalculator._extract_tag_content(text, "tag")
+        assert result == "<tag>first</tag>"
+
+
+class TestExtractSystemComponents:
+    """Tests for the extract_system_components method"""
+
+    def test_extracts_standard_agent_sections(self):
+        """Standard agent with base_instructions, memory_blocks, and memory_metadata"""
+        system_message = """
+<base_instructions>
+Base prompt here
+</base_instructions>
+
+<memory_blocks>
+Core memory content
+</memory_blocks>
+
+<memory_metadata>
+Metadata here
+</memory_metadata>
+"""
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["system_prompt"] is not None
+        assert "<base_instructions>" in result["system_prompt"]
+        assert "Base prompt here" in result["system_prompt"]
+
+        assert result["core_memory"] is not None
+        assert "Core memory content" in result["core_memory"]
+
+        assert result["external_memory_summary"] is not None
+        assert "<memory_metadata>" in result["external_memory_summary"]
+
+        # These should be None for standard agent
+        assert result["memory_filesystem"] is None
+        assert result["tool_usage_rules"] is None
+        assert result["directories"] is None
+
+    def test_extracts_git_enabled_agent_sections(self):
+        """Git-enabled agent has top-level memory_filesystem OUTSIDE memory_blocks"""
+        system_message = (
+            "<base_instructions>Base</base_instructions>\n"
+            "<memory_filesystem>\n"
+            "memory/\n"
+            "  system/\n"
+            "    human.md (100 chars)\n"
+            "</memory_filesystem>\n"
+            "<memory_metadata>Meta</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["core_memory"] is None  # git-enabled agents don't use <memory_blocks>
+        assert result["memory_filesystem"] is not None
+        assert "memory/" in result["memory_filesystem"]
+        assert "human.md" in result["memory_filesystem"]
+
+    def test_extracts_tool_usage_rules(self):
+        """Agent with tool usage rules configured"""
+        system_message = """
+<base_instructions>Base</base_instructions>
+<memory_blocks>Memory</memory_blocks>
+<tool_usage_rules>
+You must use tools in a specific order.
+</tool_usage_rules>
+<memory_metadata>Meta</memory_metadata>
+"""
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["tool_usage_rules"] is not None
+        assert "specific order" in result["tool_usage_rules"]
+
+    def test_extracts_directories(self):
+        """Agent with attached sources has directories section"""
+        system_message = """
+<base_instructions>Base</base_instructions>
+<memory_blocks>Memory</memory_blocks>
+<directories>
+<directory name="project">
+<file status="open" name="readme.md">
+README content
+</file>
+</directory>
+</directories>
+<memory_metadata>Meta</memory_metadata>
+"""
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["directories"] is not None
+        assert '<directory name="project">' in result["directories"]
+        assert "readme.md" in result["directories"]
+
+    def test_handles_react_agent_no_memory_blocks(self):
+        """React/workflow agents don't render <memory_blocks>"""
+        system_message = """
+<base_instructions>React agent base</base_instructions>
+<directories>
+Some directory content
+</directories>
+<memory_metadata>Meta</memory_metadata>
+"""
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["system_prompt"] is not None
+        assert result["core_memory"] is None  # No memory_blocks for react agents
+        assert result["directories"] is not None
+        assert result["external_memory_summary"] is not None
+
+    def test_handles_all_sections_present(self):
+        """Full agent with all optional sections"""
+        system_message = """
+<base_instructions>Base instructions</base_instructions>
+<memory_blocks>Memory blocks content</memory_blocks>
+<memory_filesystem>Filesystem tree</memory_filesystem>
+<tool_usage_rules>Tool rules</tool_usage_rules>
+<directories>Directories content</directories>
+<memory_metadata>Metadata</memory_metadata>
+"""
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["system_prompt"] is not None
+        assert result["core_memory"] is not None
+        assert result["memory_filesystem"] is not None
+        assert result["tool_usage_rules"] is not None
+        assert result["directories"] is not None
+        assert result["external_memory_summary"] is not None
+
+    def test_handles_empty_string(self):
+        """Empty input returns all None values"""
+        result = ContextWindowCalculator.extract_system_components("")
+        assert all(v is None for v in result.values())
+
+    def test_returns_correct_dict_keys(self):
+        """Verify the returned dict has all expected keys"""
+        result = ContextWindowCalculator.extract_system_components("")
+        expected_keys = {
+            "system_prompt",
+            "core_memory",
+            "memory_filesystem",
+            "tool_usage_rules",
+            "directories",
+            "external_memory_summary",
+        }
+        assert set(result.keys()) == expected_keys
+
+    def test_no_base_instructions_tag_extracts_preamble(self):
+        """Custom system prompts without <base_instructions> should extract preamble text"""
+        system_message = (
+            "You are a helpful AI agent.\n"
+            "Use the tools available to you.\n\n"
+            "<memory_blocks>\n"
+            "<persona>My name is Letta.</persona>\n"
+            "</memory_blocks>\n\n"
+            "<memory_metadata>Metadata here</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        assert result["system_prompt"] is not None
+        assert "helpful AI agent" in result["system_prompt"]
+        assert "Use the tools" in result["system_prompt"]
+        # Should NOT include memory_blocks content
+        assert "<memory_blocks>" not in result["system_prompt"]
+        assert "<memory_metadata>" not in result["system_prompt"]
+
+        assert result["core_memory"] is not None
+        assert result["external_memory_summary"] is not None
+
+    def test_nested_memory_filesystem_not_extracted_as_top_level(self):
+        """memory_filesystem block INSIDE memory_blocks should NOT be extracted as top-level"""
+        system_message = (
+            "You are a self-improving AI agent.\n\n"
+            "<memory_blocks>\n"
+            "The following memory blocks are currently engaged:\n\n"
+            "<memory_filesystem>\n"
+            "<value>\n"
+            "/memory/\n"
+            "\u251c\u2500\u2500 system/\n"
+            "\u2502   \u251c\u2500\u2500 human.md\n"
+            "\u2502   \u2514\u2500\u2500 persona.md\n"
+            "</value>\n"
+            "</memory_filesystem>\n\n"
+            "<persona>My name is Letta.</persona>\n"
+            "</memory_blocks>\n\n"
+            "<memory_metadata>Metadata</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        # memory_filesystem is nested inside memory_blocks - should NOT be extracted
+        assert result["memory_filesystem"] is None
+
+        # core_memory should include the full memory_blocks content (including the nested filesystem)
+        assert result["core_memory"] is not None
+        assert "<memory_filesystem>" in result["core_memory"]
+        assert "human.md" in result["core_memory"]
+
+    def test_top_level_memory_filesystem_outside_memory_blocks(self):
+        """Top-level memory_filesystem (git-enabled) rendered BEFORE memory_blocks is extracted"""
+        system_message = (
+            "<base_instructions>Base</base_instructions>\n"
+            "<memory_filesystem>\n"
+            "\u251c\u2500\u2500 system/\n"
+            "\u2502   \u2514\u2500\u2500 human.md\n"
+            "</memory_filesystem>\n\n"
+            "<system/human.md>\n---\ndescription: About the human\n---\nName: Alice\n</system/human.md>\n\n"
+            "<memory_metadata>Meta</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        # This memory_filesystem is top-level (no memory_blocks container)
+        assert result["memory_filesystem"] is not None
+        assert "human.md" in result["memory_filesystem"]
+
+        # Bare file blocks after </memory_filesystem> are captured as core_memory
+        assert result["core_memory"] is not None
+        assert "<system/human.md>" in result["core_memory"]
+        assert "Name: Alice" in result["core_memory"]
+
+    def test_letta_code_agent_real_format(self):
+        """Real-world Letta Code agent format: no base_instructions, nested memory_filesystem"""
+        system_message = (
+            "You are a self-improving AI agent with advanced memory.\n"
+            "You are connected to an interactive CLI tool.\n\n"
+            "# Memory\n"
+            "You have an advanced memory system.\n\n"
+            "<memory_blocks>\n"
+            "The following memory blocks are currently engaged:\n\n"
+            "<memory_filesystem>\n"
+            "<description>Filesystem view</description>\n"
+            "<value>\n"
+            "/memory/\n"
+            "\u251c\u2500\u2500 system/\n"
+            "\u2502   \u251c\u2500\u2500 human.md\n"
+            "\u2502   \u2514\u2500\u2500 persona.md\n"
+            "</value>\n"
+            "</memory_filesystem>\n\n"
+            "<persona>\n"
+            "<value>My name is Letta Code.</value>\n"
+            "</persona>\n\n"
+            "<human>\n"
+            "<value>Name: Jin Peng</value>\n"
+            "</human>\n"
+            "</memory_blocks>\n\n"
+            "<memory_metadata>\n"
+            "- The current system date is: February 10, 2026\n"
+            "- 9663 previous messages in recall memory\n"
+            "</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        # System prompt: preamble before <memory_blocks>
+        assert result["system_prompt"] is not None
+        assert "self-improving AI agent" in result["system_prompt"]
+        assert "advanced memory system" in result["system_prompt"]
+        assert "<memory_blocks>" not in result["system_prompt"]
+
+        # Core memory: the full <memory_blocks> section
+        assert result["core_memory"] is not None
+        assert "Letta Code" in result["core_memory"]
+        assert "Jin Peng" in result["core_memory"]
+
+        # memory_filesystem is NESTED inside memory_blocks - should NOT be extracted
+        assert result["memory_filesystem"] is None
+
+        # No tool_usage_rules or directories
+        assert result["tool_usage_rules"] is None
+        assert result["directories"] is None
+
+        # External memory summary
+        assert result["external_memory_summary"] is not None
+        assert "February 10, 2026" in result["external_memory_summary"]
+
+    def test_git_enabled_agent_bare_file_blocks_captured_as_core_memory(self):
+        """Git-enabled agents render bare file blocks after </memory_filesystem> — these must be captured as core_memory"""
+        system_message = (
+            "<base_instructions>Base</base_instructions>\n"
+            "<memory_filesystem>\n"
+            "\u251c\u2500\u2500 system/\n"
+            "\u2502   \u251c\u2500\u2500 human.md\n"
+            "\u2502   \u2514\u2500\u2500 persona.md\n"
+            "</memory_filesystem>\n\n"
+            "<system/human.md>\n---\ndescription: About the human\nlimit: 2000\n---\nName: Alice\n</system/human.md>\n\n"
+            "<system/persona.md>\n---\ndescription: Agent persona\n---\nI am a helpful assistant.\n</system/persona.md>\n\n"
+            "<tool_usage_rules>Always call send_message to respond.</tool_usage_rules>\n"
+            "<memory_metadata>Meta</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+
+        # memory_filesystem should be the tree view only
+        assert result["memory_filesystem"] is not None
+        assert "\u251c\u2500\u2500 system/" in result["memory_filesystem"]
+
+        # core_memory should capture the bare file blocks
+        assert result["core_memory"] is not None
+        assert "<system/human.md>" in result["core_memory"]
+        assert "Name: Alice" in result["core_memory"]
+        assert "<system/persona.md>" in result["core_memory"]
+        assert "helpful assistant" in result["core_memory"]
+
+        # tool_usage_rules should NOT be included in core_memory
+        assert "<tool_usage_rules>" not in result["core_memory"]
+
+        # Other sections
+        assert result["tool_usage_rules"] is not None
+        assert result["external_memory_summary"] is not None
+
+    def test_git_enabled_agent_no_bare_blocks(self):
+        """Git-enabled agent with no file blocks after memory_filesystem returns None for core_memory"""
+        system_message = (
+            "<base_instructions>Base</base_instructions>\n"
+            "<memory_filesystem>\n"
+            "\u251c\u2500\u2500 system/\n"
+            "</memory_filesystem>\n"
+            "<memory_metadata>Meta</memory_metadata>"
+        )
+        result = ContextWindowCalculator.extract_system_components(system_message)
+        assert result["memory_filesystem"] is not None
+        assert result["core_memory"] is None
+
+    def test_extract_top_level_tag_dual_occurrence_nested_first(self):
+        """When a tag appears nested first and top-level later, the top-level one is extracted"""
+        system_message = (
+            "<memory_blocks>\n"
+            "<tool_usage_rules>nested rules</tool_usage_rules>\n"
+            "</memory_blocks>\n\n"
+            "<tool_usage_rules>top-level rules</tool_usage_rules>"
+        )
+        result = ContextWindowCalculator._extract_top_level_tag(system_message, "tool_usage_rules")
+        assert result is not None
+        assert "top-level rules" in result
+        assert "nested rules" not in result
+
+    def test_extract_system_prompt_pure_text_no_tags(self):
+        """System message with no section tags at all returns the full text as system_prompt"""
+        system_message = "You are a simple agent.\nYou help the user with tasks."
+        result = ContextWindowCalculator._extract_system_prompt(system_message)
+        assert result is not None
+        assert "simple agent" in result
+        assert "help the user" in result
+
+    def test_git_backed_memory_without_memory_blocks_wrapper(self):
+        """Regression test from main: git-backed agents without <memory_blocks> wrapper"""
+        system_message = """You are some system prompt.
 
 <memory_filesystem>
 Memory Directory: ~/.letta/agents/agent-123/memory
 
 /memory/
-└── system/
-    └── human.md
+\u2514\u2500\u2500 system/
+    \u2514\u2500\u2500 human.md
 </memory_filesystem>
 
 <system/human.md>
@@ -26,17 +409,20 @@ hello
 - foo=bar
 </memory_metadata>
 """
+        result = ContextWindowCalculator.extract_system_components(system_message)
 
-    system_prompt, core_memory, external_memory_summary = ContextWindowCalculator.extract_system_components(system_message)
+        assert "You are some system prompt" in result["system_prompt"]
+        # memory_filesystem is a top-level section
+        assert result["memory_filesystem"] is not None
+        assert "<memory_filesystem>" in result["memory_filesystem"]
+        # bare file blocks are captured as core_memory
+        assert result["core_memory"] is not None
+        assert "<system/human.md>" in result["core_memory"]
+        assert result["external_memory_summary"].startswith("<memory_metadata>")
 
-    assert "You are some system prompt" in system_prompt
-    assert "<memory_filesystem>" in core_memory
-    assert "<system/human.md>" in core_memory
-    assert external_memory_summary.startswith("<memory_metadata>")
-
-
-def test_extract_system_components_legacy_memory_blocks_wrapper():
-    system_message = """<base_instructions>SYS</base_instructions>
+    def test_legacy_memory_blocks_wrapper(self):
+        """Regression test from main: legacy memory_blocks wrapper is properly parsed"""
+        system_message = """<base_instructions>SYS</base_instructions>
 
 <memory_blocks>
 <persona>p</persona>
@@ -46,9 +432,217 @@ def test_extract_system_components_legacy_memory_blocks_wrapper():
 - x=y
 </memory_metadata>
 """
+        result = ContextWindowCalculator.extract_system_components(system_message)
 
-    system_prompt, core_memory, external_memory_summary = ContextWindowCalculator.extract_system_components(system_message)
+        assert result["system_prompt"].startswith("<base_instructions>")
+        assert result["core_memory"].startswith("<memory_blocks>")
+        assert result["external_memory_summary"].startswith("<memory_metadata>")
 
-    assert system_prompt.startswith("<base_instructions>")
-    assert core_memory.startswith("<memory_blocks>")
-    assert external_memory_summary.startswith("<memory_metadata>")
+
+def _make_system_message(text: str):
+    """Helper to create a real Message object for use as a system message in tests."""
+    from letta.schemas.enums import MessageRole
+    from letta.schemas.letta_message_content import TextContent
+    from letta.schemas.message import Message
+
+    return Message(role=MessageRole.system, content=[TextContent(text=text)])
+
+
+def _make_mock_deps(system_text: str):
+    """Helper to create mocked token_counter, message_manager, and agent_state."""
+    token_counter = MagicMock()
+    token_counter.count_text_tokens = AsyncMock(side_effect=lambda text: len(text) if text else 0)
+    token_counter.count_message_tokens = AsyncMock(return_value=0)
+    token_counter.count_tool_tokens = AsyncMock(return_value=0)
+    token_counter.convert_messages = MagicMock(return_value=[{"role": "system", "content": system_text}])
+
+    message_manager = MagicMock()
+    message_manager.get_messages_by_ids_async = AsyncMock(return_value=[])
+
+    agent_state = MagicMock()
+    agent_state.id = "agent-test"
+    agent_state.message_ids = ["msg-sys"]
+    agent_state.system = "fallback system prompt"
+    agent_state.tools = []
+    agent_state.llm_config.context_window = 128000
+
+    actor = MagicMock()
+
+    return token_counter, message_manager, agent_state, actor
+
+
+class TestCalculateContextWindow:
+    """Integration tests for calculate_context_window with mocked dependencies"""
+
+    @pytest.mark.asyncio
+    async def test_calculate_context_window_standard_agent(self):
+        """Test full context window calculation with a standard system message"""
+        system_text = (
+            "<base_instructions>You are a helpful agent.</base_instructions>\n"
+            "<memory_blocks>human: User is Alice</memory_blocks>\n"
+            "<memory_metadata>Archival: 5 passages</memory_metadata>"
+        )
+
+        system_msg = _make_system_message(system_text)
+        token_counter, message_manager, agent_state, actor = _make_mock_deps(system_text)
+
+        calculator = ContextWindowCalculator()
+        result = await calculator.calculate_context_window(
+            agent_state=agent_state,
+            actor=actor,
+            token_counter=token_counter,
+            message_manager=message_manager,
+            system_message_compiled=system_msg,
+            num_archival_memories=5,
+            num_messages=10,
+            message_ids=[],
+        )
+
+        assert result.context_window_size_max == 128000
+        assert result.num_archival_memory == 5
+        assert result.num_recall_memory == 10
+        assert result.num_tokens_system > 0
+        assert "helpful agent" in result.system_prompt
+        assert result.num_tokens_core_memory > 0
+        assert "User is Alice" in result.core_memory
+        assert result.num_tokens_external_memory_summary > 0
+
+        # New sections should be None/0 since not in system message
+        assert result.memory_filesystem is None
+        assert result.num_tokens_memory_filesystem == 0
+        assert result.tool_usage_rules is None
+        assert result.num_tokens_tool_usage_rules == 0
+        assert result.directories is None
+        assert result.num_tokens_directories == 0
+
+    @pytest.mark.asyncio
+    async def test_calculate_context_window_skips_empty_sections(self):
+        """Verify that token counting is skipped for empty/missing sections"""
+        # Only base_instructions, no other sections
+        system_text = "<base_instructions>Simple agent</base_instructions>"
+
+        system_msg = _make_system_message(system_text)
+        token_counter, message_manager, agent_state, actor = _make_mock_deps(system_text)
+
+        calculator = ContextWindowCalculator()
+        await calculator.calculate_context_window(
+            agent_state=agent_state,
+            actor=actor,
+            token_counter=token_counter,
+            message_manager=message_manager,
+            system_message_compiled=system_msg,
+            num_archival_memories=0,
+            num_messages=0,
+            message_ids=[],
+        )
+
+        # count_text_tokens should only be called for system_prompt (non-empty)
+        # and NOT for core_memory, memory_filesystem, tool_usage_rules, directories,
+        # external_memory_summary, or summary_memory (all empty/None)
+        calls = token_counter.count_text_tokens.call_args_list
+        assert len(calls) == 1, f"Expected 1 call to count_text_tokens (system_prompt only), got {len(calls)}: {calls}"
+
+    @pytest.mark.asyncio
+    async def test_calculate_context_window_all_sections(self):
+        """Test with all optional sections present"""
+        system_text = (
+            "<base_instructions>Agent instructions</base_instructions>\n"
+            "<memory_blocks>Core memory</memory_blocks>\n"
+            "<memory_filesystem>\u251c\u2500\u2500 system/\n\u2502   \u2514\u2500\u2500 human.md</memory_filesystem>\n"
+            "<tool_usage_rules>Always call search first</tool_usage_rules>\n"
+            '<directories><directory name="docs">content</directory></directories>\n'
+            "<memory_metadata>Archival: 10 passages</memory_metadata>"
+        )
+
+        system_msg = _make_system_message(system_text)
+        token_counter, message_manager, agent_state, actor = _make_mock_deps(system_text)
+
+        calculator = ContextWindowCalculator()
+        result = await calculator.calculate_context_window(
+            agent_state=agent_state,
+            actor=actor,
+            token_counter=token_counter,
+            message_manager=message_manager,
+            system_message_compiled=system_msg,
+            num_archival_memories=10,
+            num_messages=5,
+            message_ids=[],
+        )
+
+        # All sections should be populated
+        assert result.num_tokens_system > 0
+        assert result.num_tokens_core_memory > 0
+        assert result.num_tokens_memory_filesystem > 0
+        assert result.memory_filesystem is not None
+        assert result.num_tokens_tool_usage_rules > 0
+        assert result.tool_usage_rules is not None
+        assert result.num_tokens_directories > 0
+        assert result.directories is not None
+        assert result.num_tokens_external_memory_summary > 0
+
+        # Verify total is sum of all parts
+        expected_total = (
+            result.num_tokens_system
+            + result.num_tokens_core_memory
+            + result.num_tokens_memory_filesystem
+            + result.num_tokens_tool_usage_rules
+            + result.num_tokens_directories
+            + result.num_tokens_external_memory_summary
+            + result.num_tokens_summary_memory
+            + result.num_tokens_messages
+            + result.num_tokens_functions_definitions
+        )
+        assert result.context_window_size_current == expected_total
+
+    @pytest.mark.asyncio
+    async def test_calculate_context_window_git_enabled_agent(self):
+        """Test that git-enabled agents capture bare file blocks as core_memory"""
+        system_text = (
+            "<base_instructions>Git agent</base_instructions>\n"
+            "<memory_filesystem>\n"
+            "\u251c\u2500\u2500 system/\n"
+            "\u2502   \u251c\u2500\u2500 human.md\n"
+            "\u2502   \u2514\u2500\u2500 persona.md\n"
+            "</memory_filesystem>\n\n"
+            "<system/human.md>\n---\ndescription: About the human\n---\nName: Alice\n</system/human.md>\n\n"
+            "<system/persona.md>\n---\ndescription: Agent persona\n---\nI am helpful.\n</system/persona.md>\n\n"
+            "<memory_metadata>Archival: 3 passages</memory_metadata>"
+        )
+
+        system_msg = _make_system_message(system_text)
+        token_counter, message_manager, agent_state, actor = _make_mock_deps(system_text)
+
+        calculator = ContextWindowCalculator()
+        result = await calculator.calculate_context_window(
+            agent_state=agent_state,
+            actor=actor,
+            token_counter=token_counter,
+            message_manager=message_manager,
+            system_message_compiled=system_msg,
+            num_archival_memories=3,
+            num_messages=5,
+            message_ids=[],
+        )
+
+        # memory_filesystem should capture the tree view
+        assert result.memory_filesystem is not None
+        assert result.num_tokens_memory_filesystem > 0
+
+        # core_memory should capture the bare file blocks
+        assert result.num_tokens_core_memory > 0
+        assert "Name: Alice" in result.core_memory
+        assert "<system/persona.md>" in result.core_memory
+
+        # Total should include all sections
+        expected_total = (
+            result.num_tokens_system
+            + result.num_tokens_core_memory
+            + result.num_tokens_memory_filesystem
+            + result.num_tokens_tool_usage_rules
+            + result.num_tokens_directories
+            + result.num_tokens_external_memory_summary
+            + result.num_tokens_summary_memory
+            + result.num_tokens_messages
+            + result.num_tokens_functions_definitions
+        )
+        assert result.context_window_size_current == expected_total