diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 8fff669..e8019f7 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -23,7 +23,7 @@ jobs:
           version: "latest"
 
       - name: Set up Python
-        run: uv python install 3.13
+        run: uv python install 3.14
 
       - name: Install dependencies
         run: uv sync --all-extras
@@ -46,7 +46,7 @@ jobs:
           version: "latest"
 
       - name: Set up Python
-        run: uv python install 3.13
+        run: uv python install 3.14
 
       - name: Install dependencies
         run: uv sync --all-extras
@@ -66,7 +66,7 @@ jobs:
           version: "latest"
 
       - name: Set up Python
-        run: uv python install 3.13
+        run: uv python install 3.14
 
       - name: Install dependencies
         run: uv sync --all-extras
diff --git a/CLAUDE.md b/CLAUDE.md
index 4de6144..33b8d3f 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -17,7 +17,7 @@ See [CONTRIBUTING.md](CONTRIBUTING.md) for detailed architecture, code style, an
 - Use `uv add <package>` (or `uv add --optional dev <package>`) to introduce new dependencies — this updates `pyproject.toml` and `uv.lock` together
 
 ### Python Version
-- Use Python 3.13.x (pinned in `pyproject.toml`)
+- Use Python 3.14.x (pinned in `pyproject.toml`)
 - Check version: `uv run python --version`
 
 ### Before Running Any Python Code
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 4efa95a..4c98afe 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -6,7 +6,7 @@ This guide covers development setup, architecture, and how to extend Drover.
 
 ### Prerequisites
 
-- Python 3.13.x
+- Python 3.14.x
 - [uv](https://docs.astral.sh/uv/) (package and environment manager)
 
 ### Environment Setup
diff --git a/README.md b/README.md
index ee7a0a2..602049f 100644
--- a/README.md
+++ b/README.md
@@ -35,7 +35,7 @@ Drover uses LLMs to analyze documents and suggest consistent, policy-compliant f
 
 ### Prerequisites
 
-- Python 3.13.x
+- Python 3.14.x
 - [uv](https://docs.astral.sh/uv/) (package and environment manager)
 - [Ollama](https://ollama.ai/) (for local inference) or API keys for cloud providers
 
diff --git a/docs/increments.md b/docs/increments.md
index 79e3004..94f479e 100644
--- a/docs/increments.md
+++ b/docs/increments.md
@@ -54,7 +54,7 @@ Establish automated quality gates and consistent development workflows.
 
 ### GitHub Actions CI Pipeline
 - [ ] Create workflow for lint, type-check, and test on PR
-- [ ] Add matrix testing across OS platforms (Ubuntu, macOS, Windows) with Python 3.13
+- [ ] Add matrix testing across OS platforms (Ubuntu, macOS, Windows) with Python 3.14
 - [ ] Configure dependency caching for faster builds
 - [ ] Add security scanning (pip-audit, bandit)
 - [ ] Set up coverage reporting with threshold enforcement
diff --git a/pyproject.toml b/pyproject.toml
index 045805b..41f914b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -3,7 +3,7 @@ name = "drover"
 version = "0.2.0"
 description = "Document classification CLI that classifies files into organized folder structures"
 readme = "README.md"
-requires-python = ">=3.13,<3.14"
+requires-python = ">=3.14"
 license = "AGPL-3.0-or-later"
 dependencies = [
     "langchain>=0.3,<1.0",
@@ -57,7 +57,7 @@ markers = [
 ]
 
 [tool.ruff]
-target-version = "py313"
+target-version = "py314"
 src = ["src", "tests"]
 
 [tool.ruff.lint]
@@ -90,7 +90,7 @@ known-first-party = ["drover"]
 "tests/**/*.py" = ["ARG001", "ARG002", "ERA001"]
 
 [tool.mypy]
-python_version = "3.13"
+python_version = "3.14"
 strict = true
 warn_return_any = true
 warn_unused_configs = true
diff --git a/smoke/README.md b/smoke/README.md
index f5c5cb7..8ff1366 100644
--- a/smoke/README.md
+++ b/smoke/README.md
@@ -86,7 +86,7 @@ Exit code: 0 if every non-skipped test passed; 1 if any failed.
   "duration_ms": 134812,
   "environment": {
     "drover_version": "0.1.0",
-    "python_version": "3.13.x",
+    "python_version": "3.14.x",
     "platform": "darwin",
     "ollama_available": true,
     "ollama_endpoint": "http://127.0.0.1:11434",
diff --git a/src/drover/actions/base.py b/src/drover/actions/base.py
index b04e906..967cb61 100644
--- a/src/drover/actions/base.py
+++ b/src/drover/actions/base.py
@@ -1,10 +1,12 @@
 """Base abstractions for file actions based on classification results."""
 
 from dataclasses import dataclass, field
-from pathlib import Path
-from typing import Any, Protocol
+from typing import TYPE_CHECKING, Any, Protocol
 
-from drover.models import ClassificationResult
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from drover.models import ClassificationResult
 
 
 @dataclass
diff --git a/src/drover/classifier.py b/src/drover/classifier.py
index 3f0e643..a0df5b5 100644
--- a/src/drover/classifier.py
+++ b/src/drover/classifier.py
@@ -12,19 +12,22 @@
 import os
 import re
 import socket
-from collections.abc import Callable
 from importlib.resources import files
-from pathlib import Path
 from typing import TYPE_CHECKING, Any, cast
 
 if TYPE_CHECKING:
+    from collections.abc import Callable
     from importlib.resources.abc import Traversable
+    from pathlib import Path
+
+    from langchain_core.language_models import BaseChatModel
+    from langchain_core.runnables import Runnable
+
+    from drover.taxonomy.base import BaseTaxonomy
 
 import yaml
 from json_repair import repair_json
-from langchain_core.language_models import BaseChatModel
 from langchain_core.messages import BaseMessage, HumanMessage, SystemMessage
-from langchain_core.runnables import Runnable
 from langchain_ollama import ChatOllama
 from langchain_openai import ChatOpenAI
 from pydantic import ValidationError
@@ -39,7 +42,6 @@
 from drover.logging import get_logger
 from drover.metrics import create_metrics_callback
 from drover.models import RawClassification
-from drover.taxonomy.base import BaseTaxonomy
 
 logger = get_logger(__name__)
 
diff --git a/src/drover/cli.py b/src/drover/cli.py
index be3c7f6..bc28d31 100644
--- a/src/drover/cli.py
+++ b/src/drover/cli.py
@@ -57,7 +57,7 @@ def _git_head_marker() -> str:
             text=True,
             stderr=subprocess.DEVNULL,
         ).strip()
-    except (subprocess.CalledProcessError, FileNotFoundError, OSError):
+    except subprocess.CalledProcessError, FileNotFoundError, OSError:
         return ""
     try:
         dirty = (
@@ -68,7 +68,7 @@ def _git_head_marker() -> str:
             ).returncode
             != 0
         )
-    except (FileNotFoundError, OSError):
+    except FileNotFoundError, OSError:
         dirty = False
     return f"{head}-dirty" if dirty else head
 
diff --git a/src/drover/evaluation.py b/src/drover/evaluation.py
index a5c8faa..27ce8c9 100644
--- a/src/drover/evaluation.py
+++ b/src/drover/evaluation.py
@@ -10,17 +10,20 @@
 """
 
 import json
-from collections.abc import Sequence
 from dataclasses import dataclass, field
 from pathlib import Path
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
 from pydantic import BaseModel, Field
 
-from drover.classifier import DocumentClassifier
-from drover.loader import DoclingLoader
 from drover.logging import get_logger
-from drover.models import RawClassification
+
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from drover.classifier import DocumentClassifier
+    from drover.loader import DoclingLoader
+    from drover.models import RawClassification
 
 logger = get_logger(__name__)
 
diff --git a/src/drover/metrics.py b/src/drover/metrics.py
index 02812e6..512bf51 100644
--- a/src/drover/metrics.py
+++ b/src/drover/metrics.py
@@ -5,12 +5,14 @@
 """
 
 import time
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
 from langchain_core.callbacks import BaseCallbackHandler
-from langchain_core.outputs import LLMResult
 from pydantic import BaseModel, Field
 
+if TYPE_CHECKING:
+    from langchain_core.outputs import LLMResult
+
 MODEL_PRICING: dict[str, tuple[float, float]] = {
     "gpt-4o": (2.50, 10.00),
     "gpt-4o-mini": (0.15, 0.60),
diff --git a/src/drover/models.py b/src/drover/models.py
index 1e0a823..316c8a2 100644
--- a/src/drover/models.py
+++ b/src/drover/models.py
@@ -1,11 +1,13 @@
 """Pydantic models for document classification."""
 
 from enum import StrEnum
-from pathlib import Path
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
 from pydantic import BaseModel, Field
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
 
 class ErrorCode(StrEnum):
     """Error codes for classification failures."""
@@ -65,7 +67,7 @@ class ClassificationErrorResult(BaseModel):
     @classmethod
     def from_exception(
         cls, filename: str | Path, code: ErrorCode, exception: Exception
-    ) -> "ClassificationErrorResult":
+    ) -> ClassificationErrorResult:
         """Create error result from an exception."""
         return cls(
             original=str(filename),
diff --git a/src/drover/naming/loader.py b/src/drover/naming/loader.py
index 93ae46e..b45202d 100644
--- a/src/drover/naming/loader.py
+++ b/src/drover/naming/loader.py
@@ -1,8 +1,12 @@
 """Naming policy plugin discovery and loading."""
 
-from drover.naming.base import BaseNamingPolicy
+from typing import TYPE_CHECKING
+
 from drover.naming.nara import NARAPolicyNaming
 
+if TYPE_CHECKING:
+    from drover.naming.base import BaseNamingPolicy
+
 _BUILTIN_POLICIES: dict[str, type[BaseNamingPolicy]] = {
     "nara": NARAPolicyNaming,
 }
diff --git a/src/drover/path_builder.py b/src/drover/path_builder.py
index 4e83b5a..b793995 100644
--- a/src/drover/path_builder.py
+++ b/src/drover/path_builder.py
@@ -7,11 +7,15 @@
 """
 
 import re
-from pathlib import Path
+from typing import TYPE_CHECKING
 
 from drover.models import ClassificationResult, PathConstraints, RawClassification
-from drover.naming.base import BaseNamingPolicy
-from drover.taxonomy.base import BaseTaxonomy
+
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from drover.naming.base import BaseNamingPolicy
+    from drover.taxonomy.base import BaseTaxonomy
 
 
 class PathConstraintError(Exception):
diff --git a/src/drover/taxonomy/loader.py b/src/drover/taxonomy/loader.py
index d23a5b3..ffba244 100644
--- a/src/drover/taxonomy/loader.py
+++ b/src/drover/taxonomy/loader.py
@@ -1,8 +1,12 @@
 """Taxonomy plugin discovery and loading."""
 
-from drover.taxonomy.base import BaseTaxonomy
+from typing import TYPE_CHECKING
+
 from drover.taxonomy.household import HouseholdTaxonomy
 
+if TYPE_CHECKING:
+    from drover.taxonomy.base import BaseTaxonomy
+
 _BUILTIN_TAXONOMIES: dict[str, type[BaseTaxonomy]] = {
     "household": HouseholdTaxonomy,
 }
diff --git a/tests/integration/test_classify_pipeline.py b/tests/integration/test_classify_pipeline.py
index 11e01c6..4f174b0 100644
--- a/tests/integration/test_classify_pipeline.py
+++ b/tests/integration/test_classify_pipeline.py
@@ -7,16 +7,19 @@
 """
 
 from pathlib import Path
+from typing import TYPE_CHECKING
 
 import pytest
 
-from drover.classifier import DocumentClassifier
-from drover.loader import DoclingLoader
 from drover.models import RawClassification
 from drover.naming.nara import NARAPolicyNaming
 from drover.path_builder import PathBuilder
 from drover.taxonomy.household import HouseholdTaxonomy
 
+if TYPE_CHECKING:
+    from drover.classifier import DocumentClassifier
+    from drover.loader import DoclingLoader
+
 
 @pytest.mark.integration
 class TestClassificationPipeline:
diff --git a/tests/test_actions_base.py b/tests/test_actions_base.py
index 1df8d61..1c7a8b3 100644
--- a/tests/test_actions_base.py
+++ b/tests/test_actions_base.py
@@ -1,14 +1,16 @@
 """Tests for the action infrastructure."""
 
 from pathlib import Path
-
-import pytest
+from typing import TYPE_CHECKING
 
 from drover.actions.base import ActionPlan, ActionResult
 from drover.actions.runner import ActionRunner
 from drover.config import DroverConfig, ErrorMode
 from drover.models import ClassificationResult
 
+if TYPE_CHECKING:
+    import pytest
+
 
 class MockAction:
     """Mock action for testing."""
diff --git a/tests/test_classifier_docling.py b/tests/test_classifier_docling.py
index 7b6d260..24f3026 100644
--- a/tests/test_classifier_docling.py
+++ b/tests/test_classifier_docling.py
@@ -4,13 +4,16 @@
 that the max_prompt_chars cap is applied correctly.
 """
 
-import pytest
+from typing import TYPE_CHECKING
 
 from drover.classifier import DocumentClassifier
 from drover.config import AIProvider, TaxonomyMode
 from drover.models import RawClassification
 from drover.taxonomy.household import HouseholdTaxonomy
 
+if TYPE_CHECKING:
+    import pytest
+
 
 class _StubStructuredLLM:
     """Records the messages passed to the structured LLM."""
diff --git a/tests/test_service_debug_structure.py b/tests/test_service_debug_structure.py
index 9dddd87..3df30d8 100644
--- a/tests/test_service_debug_structure.py
+++ b/tests/test_service_debug_structure.py
@@ -6,14 +6,17 @@
 """
 
 import json
-from pathlib import Path
 from types import SimpleNamespace
+from typing import TYPE_CHECKING
 from unittest.mock import patch
 
-import pytest
-
 from drover.loader import DoclingLoader, LoadedDocument
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    import pytest
+
 
 def _patch_classifier(service: object, monkeypatch: pytest.MonkeyPatch) -> None:
     """Replace the classifier with a no-op fake so tests stay LLM-free."""
diff --git a/tests/test_tag_manager.py b/tests/test_tag_manager.py
index e61a54d..6a1834c 100644
--- a/tests/test_tag_manager.py
+++ b/tests/test_tag_manager.py
@@ -1,7 +1,7 @@
 """Tests for TagManager and tag operations."""
 
 import sys
-from pathlib import Path
+from typing import TYPE_CHECKING
 
 import pytest
 
@@ -14,6 +14,9 @@
 )
 from drover.models import ClassificationResult
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
 # Skip all tests in this module on non-macOS platforms
 pytestmark = pytest.mark.skipif(
     sys.platform != "darwin",
diff --git a/uv.lock b/uv.lock
index 58eee9e..7a54ff3 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1,15 +1,18 @@
 version = 1
 revision = 3
-requires-python = "==3.13.*"
+requires-python = ">=3.14"
 resolution-markers = [
-    "sys_platform == 'darwin'",
-    "platform_machine == 'aarch64' and sys_platform == 'linux'",
-    "(platform_machine != 'aarch64' and sys_platform == 'linux') or (sys_platform != 'darwin' and sys_platform != 'linux')",
+    "python_full_version >= '3.15' and sys_platform == 'win32'",
+    "python_full_version >= '3.15' and sys_platform == 'emscripten'",
+    "python_full_version >= '3.15' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version < '3.15' and sys_platform == 'win32'",
+    "python_full_version < '3.15' and sys_platform == 'emscripten'",
+    "python_full_version < '3.15' and sys_platform != 'emscripten' and sys_platform != 'win32'",
 ]
 
 [[package]]
 name = "accelerate"
-version = "1.12.0"
+version = "1.13.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "huggingface-hub" },
@@ -20,9 +23,9 @@ dependencies = [
     { name = "safetensors" },
     { name = "torch" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/4a/8e/ac2a9566747a93f8be36ee08532eb0160558b07630a081a6056a9f89bf1d/accelerate-1.12.0.tar.gz", hash = "sha256:70988c352feb481887077d2ab845125024b2a137a5090d6d7a32b57d03a45df6", size = 398399, upload-time = "2025-11-21T11:27:46.973Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/ca/14/787e5498cd062640f0f3d92ef4ae4063174f76f9afd29d13fc52a319daae/accelerate-1.13.0.tar.gz", hash = "sha256:d631b4e0f5b3de4aff2d7e9e6857d164810dfc3237d54d017f075122d057b236", size = 402835, upload-time = "2026-03-04T19:34:12.359Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/9f/d2/c581486aa6c4fbd7394c23c47b83fa1a919d34194e16944241daf9e762dd/accelerate-1.12.0-py3-none-any.whl", hash = "sha256:3e2091cd341423207e2f084a6654b1efcd250dc326f2a37d6dde446e07cabb11", size = 380935, upload-time = "2025-11-21T11:27:44.522Z" },
+    { url = "https://files.pythonhosted.org/packages/7e/46/02ac5e262d4af18054b3e922b2baedbb2a03289ee792162de60a865defc5/accelerate-1.13.0-py3-none-any.whl", hash = "sha256:cf1a3efb96c18f7b152eb0fa7490f3710b19c3f395699358f08decca2b8b62e0", size = 383744, upload-time = "2026-03-04T19:34:10.313Z" },
 ]
 
 [[package]]
@@ -45,7 +48,7 @@ wheels = [
 
 [[package]]
 name = "anthropic"
-version = "0.75.0"
+version = "0.102.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
@@ -57,9 +60,9 @@ dependencies = [
     { name = "sniffio" },
     { name = "typing-extensions" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/04/1f/08e95f4b7e2d35205ae5dcbb4ae97e7d477fc521c275c02609e2931ece2d/anthropic-0.75.0.tar.gz", hash = "sha256:e8607422f4ab616db2ea5baacc215dd5f028da99ce2f022e33c7c535b29f3dfb", size = 439565, upload-time = "2025-11-24T20:41:45.28Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/b9/47/cb2a71f70431fb09af4db83e3ea89eb2dd8e0e348d27af53ed32e6c599dd/anthropic-0.102.0.tar.gz", hash = "sha256:96f747cad11886c4ae12d4080131b94eebd68b202bd2190fe27959031bb1fa9c", size = 763697, upload-time = "2026-05-13T18:12:41.624Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/60/1c/1cd02b7ae64302a6e06724bf80a96401d5313708651d277b1458504a1730/anthropic-0.75.0-py3-none-any.whl", hash = "sha256:ea8317271b6c15d80225a9f3c670152746e88805a7a61e14d4a374577164965b", size = 388164, upload-time = "2025-11-24T20:41:43.587Z" },
+    { url = "https://files.pythonhosted.org/packages/87/75/0f6c603594876413bc858a00e7cc0d80a0cc14edf5c7b959a3ea6ec45e44/anthropic-0.102.0-py3-none-any.whl", hash = "sha256:ab96540bbd4b0f36564252d955a86f8abbe4f00944a24bc9931acc9b139bab6f", size = 763070, upload-time = "2026-05-13T18:12:43.474Z" },
 ]
 
 [[package]]
@@ -70,14 +73,52 @@ sdist = { url = "https://files.pythonhosted.org/packages/3e/38/7859ff46355f76f8d
 
 [[package]]
 name = "anyio"
-version = "4.12.0"
+version = "4.13.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "idna" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/16/ce/8a777047513153587e5434fd752e89334ac33e379aa3497db860eeb60377/anyio-4.12.0.tar.gz", hash = "sha256:73c693b567b0c55130c104d0b43a9baf3aa6a31fc6110116509f27bf75e21ec0", size = 228266, upload-time = "2025-11-28T23:37:38.911Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/7f/9c/36c5c37947ebfb8c7f22e0eb6e4d188ee2d53aa3880f3f2744fb894f0cb1/anyio-4.12.0-py3-none-any.whl", hash = "sha256:dad2376a628f98eeca4881fc56cd06affd18f659b17a747d3ff0307ced94b1bb", size = 113362, upload-time = "2025-11-28T23:36:57.897Z" },
+sdist = { url = "https://files.pythonhosted.org/packages/19/14/2c5dd9f512b66549ae92767a9c7b330ae88e1932ca57876909410251fe13/anyio-4.13.0.tar.gz", hash = "sha256:334b70e641fd2221c1505b3890c69882fe4a2df910cba14d97019b90b24439dc", size = 231622, upload-time = "2026-03-24T12:59:09.671Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/da/42/e921fccf5015463e32a3cf6ee7f980a6ed0f395ceeaa45060b61d86486c2/anyio-4.13.0-py3-none-any.whl", hash = "sha256:08b310f9e24a9594186fd75b4f73f4a4152069e3853f1ed8bfbf58369f4ad708", size = 114353, upload-time = "2026-03-24T12:59:08.246Z" },
+]
+
+[[package]]
+name = "ast-serialize"
+version = "0.4.0"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/e2/1f/50f241d4e01fe75f4bba6a209edd4047c4b26acf70992ff885fd161f79cb/ast_serialize-0.4.0.tar.gz", hash = "sha256:74e4e634ab82d1466acf0be27043178570b98ebeaa3165f9240a6fad4c286471", size = 60687, upload-time = "2026-05-14T22:44:38.251Z" }
+wheels = [
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