diff --git a/src/basic_memory/schemas/base.py b/src/basic_memory/schemas/base.py
index 142a23ab..5219fdc8 100644
--- a/src/basic_memory/schemas/base.py
+++ b/src/basic_memory/schemas/base.py
@@ -21,13 +21,38 @@
 from annotated_types import MinLen, MaxLen
 from dateparser import parse
 
-from pydantic import BaseModel, BeforeValidator, Field, model_validator
+from pydantic import BaseModel, BeforeValidator, Field, model_validator, computed_field
 
 from basic_memory.config import ConfigManager
 from basic_memory.file_utils import sanitize_for_filename, sanitize_for_folder
 from basic_memory.utils import generate_permalink
 
 
+def has_valid_file_extension(filename: str) -> bool:
+    """Check if a filename has a valid file extension recognized by mimetypes.
+
+    This is used to determine whether to split the extension when processing
+    titles in kebab_filenames mode. Prevents treating periods in version numbers
+    or decimals as file extensions.
+
+    Args:
+        filename: The filename to check
+
+    Returns:
+        True if the filename has a recognized file extension, False otherwise
+
+    Examples:
+        >>> has_valid_file_extension("document.md")
+        True
+        >>> has_valid_file_extension("Version 2.0.0")
+        False
+        >>> has_valid_file_extension("image.png")
+        True
+    """
+    mime_type, _ = mimetypes.guess_type(filename)
+    return mime_type is not None
+
+
 def to_snake_case(name: str) -> str:
     """Convert a string to snake_case.
 
@@ -232,12 +257,17 @@ def safe_title(self) -> str:
         use_kebab_case = app_config.kebab_filenames
 
         if use_kebab_case:
-            fixed_title = generate_permalink(file_path=fixed_title, split_extension=False)
+            # Convert to kebab-case: lowercase with hyphens, preserving periods in version numbers
+            # generate_permalink() uses mimetypes to detect real file extensions and only splits
+            # them off, avoiding misinterpreting periods in version numbers as extensions
+            has_extension = has_valid_file_extension(fixed_title)
+            fixed_title = generate_permalink(file_path=fixed_title, split_extension=has_extension)
 
         return fixed_title
 
+    @computed_field
     @property
-    def file_path(self):
+    def file_path(self) -> str:
         """Get the file path for this entity based on its permalink."""
         safe_title = self.safe_title
         if self.content_type == "text/markdown":
diff --git a/src/basic_memory/utils.py b/src/basic_memory/utils.py
index 15078e1f..d18526d7 100644
--- a/src/basic_memory/utils.py
+++ b/src/basic_memory/utils.py
@@ -76,10 +76,14 @@ def generate_permalink(file_path: Union[Path, str, PathLike], split_extension: b
 
     Args:
         file_path: Original file path (str, Path, or PathLike)
+        split_extension: Whether to split off and discard file extensions.
+                        When True, uses mimetypes to detect real extensions.
+                        When False, preserves all content including periods.
 
     Returns:
         Normalized permalink that matches validation rules. Converts spaces and underscores
         to hyphens for consistency. Preserves non-ASCII characters like Chinese.
+        Preserves periods in version numbers (e.g., "2.0.0") when they're not real file extensions.
 
     Examples:
         >>> generate_permalink("docs/My Feature.md")
@@ -90,12 +94,25 @@ def generate_permalink(file_path: Union[Path, str, PathLike], split_extension: b
         'design/unified-model-refactor'
         >>> generate_permalink("中文/测试文档.md")
         '中文/测试文档'
+        >>> generate_permalink("Version 2.0.0")
+        'version-2.0.0'
     """
     # Convert Path to string if needed
     path_str = Path(str(file_path)).as_posix()
 
-    # Remove extension (for now, possibly)
-    (base, extension) = os.path.splitext(path_str)
+    # Only split extension if there's a real file extension
+    # Use mimetypes to detect real extensions, avoiding misinterpreting periods in version numbers
+    import mimetypes
+    mime_type, _ = mimetypes.guess_type(path_str)
+    has_real_extension = mime_type is not None
+
+    if has_real_extension and split_extension:
+        # Real file extension detected - split it off
+        (base, extension) = os.path.splitext(path_str)
+    else:
+        # No real extension or split_extension=False - process the whole string
+        base = path_str
+        extension = ""
 
     # Check if we have CJK characters that should be preserved
     # CJK ranges: \u4e00-\u9fff (CJK Unified Ideographs), \u3000-\u303f (CJK symbols),
@@ -147,9 +164,9 @@ def generate_permalink(file_path: Union[Path, str, PathLike], split_extension: b
         # Remove apostrophes entirely (don't replace with hyphens)
         text_no_apostrophes = text_with_hyphens.replace("'", "")
 
-        # Replace unsafe chars with hyphens, but preserve CJK characters
+        # Replace unsafe chars with hyphens, but preserve CJK characters and periods
         clean_text = re.sub(
-            r"[^a-z0-9\u4e00-\u9fff\u3000-\u303f\u3400-\u4dbf/\-]", "-", text_no_apostrophes
+            r"[^a-z0-9\u4e00-\u9fff\u3000-\u303f\u3400-\u4dbf/\-\.]", "-", text_no_apostrophes
         )
     else:
         # Original ASCII-only processing for backward compatibility
@@ -168,8 +185,8 @@ def generate_permalink(file_path: Union[Path, str, PathLike], split_extension: b
         # Remove apostrophes entirely (don't replace with hyphens)
         text_no_apostrophes = text_with_hyphens.replace("'", "")
 
-        # Replace remaining invalid chars with hyphens
-        clean_text = re.sub(r"[^a-z0-9/\-]", "-", text_no_apostrophes)
+        # Replace remaining invalid chars with hyphens, preserving periods
+        clean_text = re.sub(r"[^a-z0-9/\-\.]", "-", text_no_apostrophes)
 
     # Collapse multiple hyphens
     clean_text = re.sub(r"-+", "-", clean_text)
diff --git a/tests/mcp/test_tool_write_note_kebab_filenames.py b/tests/mcp/test_tool_write_note_kebab_filenames.py
new file mode 100644
index 00000000..4e86ee69
--- /dev/null
+++ b/tests/mcp/test_tool_write_note_kebab_filenames.py
@@ -0,0 +1,392 @@
+"""Comprehensive test suite for kebab_filenames configuration.
+
+Tests the BASIC_MEMORY_KEBAB_FILENAMES configuration option which controls
+whether note filenames are converted to kebab-case (lowercase with hyphens).
+
+Feature added in PR #260 to handle forward slashes in filenames.
+This test suite was expanded to comprehensively test all kebab-case transformations.
+
+Key behaviors tested:
+1. When kebab_filenames=true: All special characters, spaces, periods, underscores,
+   and mixed case are converted to lowercase kebab-case
+2. When kebab_filenames=false: Original formatting is preserved (backward compatibility)
+3. Folder paths are not affected by kebab_filenames setting
+4. Permalinks are always kebab-case regardless of kebab_filenames setting
+"""
+
+import pytest
+from basic_memory.mcp.tools import write_note
+from basic_memory.config import ConfigManager
+
+
+# =============================================================================
+# Basic Transformations (kebab_filenames=true)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_spaces_to_hyphens(app, test_project, app_config):
+    """Test that spaces are converted to hyphens when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="My Awesome Note",
+        folder="test",
+        content="Testing space conversion",
+    )
+
+    assert "file_path: test/my-awesome-note.md" in result
+    assert "permalink: test/my-awesome-note" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_underscores_to_hyphens(app, test_project, app_config):
+    """Test that underscores are converted to hyphens when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="my_note_with_underscores",
+        folder="test",
+        content="Testing underscore conversion",
+    )
+
+    assert "file_path: test/my-note-with-underscores.md" in result
+    assert "permalink: test/my-note-with-underscores" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_camelcase_to_kebab(app, test_project, app_config):
+    """Test that CamelCase is converted to kebab-case when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="MyAwesomeFeature",
+        folder="test",
+        content="Testing CamelCase conversion",
+    )
+
+    assert "file_path: test/my-awesome-feature.md" in result
+    assert "permalink: test/my-awesome-feature" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_mixed_case_to_lowercase(app, test_project, app_config):
+    """Test that mixed case is converted to lowercase when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="MIXED_Case_Example",
+        folder="test",
+        content="Testing case conversion",
+    )
+
+    assert "file_path: test/mixed-case-example.md" in result
+    assert "permalink: test/mixed-case-example" in result
+
+
+# =============================================================================
+# Period Handling (kebab_filenames=true)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_single_period_preserved(app, test_project, app_config):
+    """Test that periods in version numbers are preserved when kebab_filenames=true.
+
+    This preserves semantic meaning of version numbers like "3.0" while still
+    converting spaces to hyphens. Only actual file extensions are split off.
+    """
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Test 3.0 Version",
+        folder="test",
+        content="Testing period preservation",
+    )
+
+    assert "file_path: test/test-3.0-version.md" in result
+    assert "permalink: test/test-3.0-version" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_multiple_periods_preserved(app, test_project, app_config):
+    """Test that multiple periods in version numbers are preserved when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Version 1.2.3 Release",
+        folder="test",
+        content="Testing multiple period preservation",
+    )
+
+    assert "file_path: test/version-1.2.3-release.md" in result
+    assert "permalink: test/version-1.2.3-release" in result
+
+
+# =============================================================================
+# Special Characters (kebab_filenames=true)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_special_chars_to_hyphens(app, test_project, app_config):
+    """Test that special characters are converted while preserving periods in version numbers."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Test 2.0: New Feature",
+        folder="test",
+        content="Testing special character conversion",
+    )
+
+    assert "file_path: test/test-2.0-new-feature.md" in result
+    assert "permalink: test/test-2.0-new-feature" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_parentheses_removed(app, test_project, app_config):
+    """Test that parentheses are handled while preserving periods in version numbers."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Feature (v2.0) Update",
+        folder="test",
+        content="Testing parentheses handling",
+    )
+
+    assert "file_path: test/feature-v2.0-update.md" in result
+    assert "permalink: test/feature-v2.0-update" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_apostrophes_removed(app, test_project, app_config):
+    """Test that apostrophes are removed when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="User's Guide",
+        folder="test",
+        content="Testing apostrophe handling",
+    )
+
+    assert "file_path: test/users-guide.md" in result
+    assert "permalink: test/users-guide" in result
+
+
+# =============================================================================
+# Combined Transformations (kebab_filenames=true)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_all_transformations_combined(app, test_project, app_config):
+    """Test multiple transformation types combined while preserving periods in version numbers."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="MyProject_v3.0: Feature Update (DRAFT)",
+        folder="test",
+        content="Testing combined transformations",
+    )
+
+    assert "file_path: test/my-project-v3.0-feature-update-draft.md" in result
+    assert "permalink: test/my-project-v3.0-feature-update-draft" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_consecutive_special_chars_collapsed(app, test_project, app_config):
+    """Test that consecutive special characters collapse to single hyphen."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Test___Multiple---Separators",
+        folder="test",
+        content="Testing consecutive special character collapse",
+    )
+
+    # Multiple underscores/hyphens should collapse to single hyphen
+    assert "file_path: test/test-multiple-separators.md" in result
+    assert "permalink: test/test-multiple-separators" in result
+
+
+# =============================================================================
+# Edge Cases (kebab_filenames=true)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_leading_trailing_hyphens_trimmed(app, test_project, app_config):
+    """Test that leading/trailing hyphens are trimmed when kebab_filenames=true."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="---Test Note---",
+        folder="test",
+        content="Testing leading/trailing hyphen trimming",
+    )
+
+    assert "file_path: test/test-note.md" in result
+    assert "permalink: test/test-note" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_all_special_chars_becomes_valid_filename(app, test_project, app_config):
+    """Test that a title with mostly special characters becomes valid."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="!!!Test!!!",
+        folder="test",
+        content="Testing all special characters",
+    )
+
+    assert "file_path: test/test.md" in result
+    assert "permalink: test/test" in result
+
+
+# =============================================================================
+# Folder Path Handling (kebab_filenames=true)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_folder_path_unaffected(app, test_project, app_config):
+    """Test that folder paths are NOT affected by kebab_filenames setting."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Test Note",
+        folder="My_Folder/Sub Folder",  # Folder should remain as-is
+        content="Testing folder path preservation",
+    )
+
+    # Folder paths should be preserved (sanitized but not kebab-cased)
+    assert "file_path: My_Folder/Sub Folder/test-note.md" in result
+    assert "permalink: my-folder/sub-folder/test-note" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_root_folder_with_kebab(app, test_project, app_config):
+    """Test kebab_filenames preserves periods in version numbers with root folder."""
+    ConfigManager().config.kebab_filenames = True
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Test 3.0 Note",
+        folder="",  # Root folder
+        content="Testing root folder",
+    )
+
+    assert "file_path: test-3.0-note.md" in result
+    assert "permalink: test-3.0-note" in result
+
+
+# =============================================================================
+# Backward Compatibility (kebab_filenames=false)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_write_note_kebab_disabled_preserves_original(app, test_project, app_config):
+    """Test that original formatting is preserved when kebab_filenames=false."""
+    ConfigManager().config.kebab_filenames = False
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="Test 3.0 Version",
+        folder="test",
+        content="Testing backward compatibility",
+    )
+
+    # Periods and spaces should be preserved
+    assert "file_path: test/Test 3.0 Version.md" in result
+    # Permalinks are ALWAYS kebab-case regardless of setting, and preserve periods
+    assert "permalink: test/test-3.0-version" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_kebab_disabled_preserves_underscores(app, test_project, app_config):
+    """Test that underscores are preserved when kebab_filenames=false."""
+    ConfigManager().config.kebab_filenames = False
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="my_note_example",
+        folder="test",
+        content="Testing underscore preservation",
+    )
+
+    assert "file_path: test/my_note_example.md" in result
+    assert "permalink: test/my-note-example" in result
+
+
+@pytest.mark.asyncio
+async def test_write_note_kebab_disabled_preserves_case(app, test_project, app_config):
+    """Test that case is preserved when kebab_filenames=false."""
+    ConfigManager().config.kebab_filenames = False
+
+    result = await write_note.fn(
+        project=test_project.name,
+        title="MyAwesomeNote",
+        folder="test",
+        content="Testing case preservation",
+    )
+
+    assert "file_path: test/MyAwesomeNote.md" in result
+    assert "permalink: test/my-awesome-note" in result
+
+
+# =============================================================================
+# Permalink Consistency (both modes)
+# =============================================================================
+
+
+@pytest.mark.asyncio
+async def test_permalinks_always_kebab_case(app, test_project, app_config):
+    """Test that permalinks are ALWAYS kebab-case regardless of kebab_filenames setting.
+
+    This is important: even when kebab_filenames=false (preserving filename formatting),
+    permalinks should still be kebab-case for URL consistency. Both modes preserve periods
+    in version numbers.
+    """
+    # Test with kebab disabled
+    ConfigManager().config.kebab_filenames = False
+
+    result1 = await write_note.fn(
+        project=test_project.name,
+        title="Test Note 1",
+        folder="test",
+        content="Testing permalink consistency",
+    )
+
+    # Filename preserves original, permalink is kebab-case
+    assert "file_path: test/Test Note 1.md" in result1
+    assert "permalink: test/test-note-1" in result1
+
+    # Test with kebab enabled
+    ConfigManager().config.kebab_filenames = True
+
+    result2 = await write_note.fn(
+        project=test_project.name,
+        title="Test Note 2",
+        folder="test",
+        content="Testing permalink consistency",
+    )
+
+    # Both filename and permalink are kebab-case
+    assert "file_path: test/test-note-2.md" in result2
+    assert "permalink: test/test-note-2" in result2