diff --git a/.github/workflows/ci.txt b/.github/workflows/ci.txt
index 065e23e..73df9ab 100644
--- a/.github/workflows/ci.txt
+++ b/.github/workflows/ci.txt
@@ -1,12 +1,18 @@
 #
-# This file is autogenerated by pip-compile with python 3.11
-# To update, run:
+# This file is autogenerated by pip-compile with Python 3.11
+# by the following command:
 #
 #    pip-compile .github/workflows/ci.in
 #
-pydantic==1.10.4
-    # via -r .github/workflows/ci.in
-pypdf==3.3.0
+annotated-types==0.6.0
+    # via pydantic
+pydantic==2.5.0
     # via -r .github/workflows/ci.in
-typing-extensions==4.4.0
+pydantic-core==2.14.1
     # via pydantic
+pypdf==3.17.0
+    # via -r .github/workflows/ci.in
+typing-extensions==4.8.0
+    # via
+    #   pydantic
+    #   pydantic-core
diff --git a/.github/workflows/json_consistency.py b/.github/workflows/json_consistency.py
index c7bec8a..1383bb6 100644
--- a/.github/workflows/json_consistency.py
+++ b/.github/workflows/json_consistency.py
@@ -1,5 +1,6 @@
 import datetime
 import json
+import logging
 import sys
 from pathlib import Path
 
@@ -7,13 +8,17 @@
 
 from pypdf import PdfReader
 
+logger = logging.getLogger()
+
+logger.level = logging.ERROR
+
 
 class AnnotationCount(BaseModel):
-    Highlight: int | None
-    Ink: int | None
-    Link: int | None
-    Text: int | None
-    Widget: int | None
+    Highlight: int | None = None
+    Ink: int | None = None
+    Link: int | None = None
+    Text: int | None = None
+    Widget: int | None = None
 
     def items(self) -> list[tuple[str, int]]:
         return [
@@ -47,7 +52,7 @@ def main() -> None:
     """Check the consistency of the JSON metadata file."""
     with open("files.json") as f:
         data = json.load(f)
-    main_pdf = MainPdfFile.parse_obj(data)
+    main_pdf = MainPdfFile.model_validate(data)
     registered_pdfs = []
 
     seen_failure = False
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index f2f6d5c..0e34938 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -1,7 +1,7 @@
 # pre-commit run --all-files
 repos:
 -   repo: https://github.com/pre-commit/pre-commit-hooks
-    rev: v4.1.0
+    rev: v4.5.0
     hooks:
     -   id: check-ast
     -   id: check-case-conflict
@@ -20,21 +20,21 @@ repos:
     hooks:
     -   id: isort
 -   repo: https://github.com/psf/black
-    rev: 22.1.0
+    rev: 22.3.0
     hooks:
     -   id: black
 -   repo: https://github.com/asottile/pyupgrade
-    rev: v2.31.1
+    rev: v3.15.0
     hooks:
     -   id: pyupgrade
         args: [--py39-plus]
 -   repo: https://github.com/asottile/blacken-docs
-    rev: v1.12.1
+    rev: 1.16.0
     hooks:
     -   id: blacken-docs
         additional_dependencies: [black==22.1.0]
 -   repo: https://github.com/charliermarsh/ruff-pre-commit
-    rev: 'v0.0.280'
+    rev: 'v0.1.5'
     hooks:
     -   id: ruff
         args: ['--fix']
diff --git a/025-attachment/add_attachment.py b/025-attachment/add_attachment.py
new file mode 100644
index 0000000..d6a58d5
--- /dev/null
+++ b/025-attachment/add_attachment.py
@@ -0,0 +1,10 @@
+from pypdf import PdfReader, PdfWriter
+
+reader = PdfReader("../001-trivial/minimal-document.pdf")
+writer = PdfWriter()
+writer.append_pages_from_reader(reader)
+
+with open("image.png", "rb") as file:
+    writer.add_attachment("image.png", file.read())
+with open("with-attachment.pdf", "wb") as file:
+    writer.write(file)
diff --git a/025-attachment/image.png b/025-attachment/image.png
new file mode 100644
index 0000000..7d74f9a
Binary files /dev/null and b/025-attachment/image.png differ
diff --git a/025-attachment/with-attachment.pdf b/025-attachment/with-attachment.pdf
new file mode 100644
index 0000000..c54c152
Binary files /dev/null and b/025-attachment/with-attachment.pdf differ
diff --git a/Makefile b/Makefile
new file mode 100644
index 0000000..b30d534
--- /dev/null
+++ b/Makefile
@@ -0,0 +1,2 @@
+maint:
+	pip-compile .github/workflows/ci.in --upgrade
diff --git a/files.json b/files.json
index ce93bbc..9ea5554 100644
--- a/files.json
+++ b/files.json
@@ -317,6 +317,16 @@
                 "Highlight": 1,
                 "Ink": 1
             }
+        },
+        {
+            "path": "025-attachment/with-attachment.pdf",
+            "producer": "pypdf",
+            "creation_date": null,
+            "encrypted": false,
+            "pages": 1,
+            "images": 1,
+            "forms": 0,
+            "annotations": {}
         }
     ]
-}
\ No newline at end of file
+}