diff --git a/acquire/outputs/tar.py b/acquire/outputs/tar.py
index 69b72906..73237d25 100644
--- a/acquire/outputs/tar.py
+++ b/acquire/outputs/tar.py
@@ -1,6 +1,8 @@
 from __future__ import annotations
 
+import copy
 import io
+import shutil
 import tarfile
 from typing import TYPE_CHECKING, BinaryIO
 
@@ -100,7 +102,52 @@ def write(
             if stat:
                 info.mtime = stat.st_mtime
 
-        self.tar.addfile(info, fh)
+        # Inline version of Python stdlib's tarfile.addfile & tarfile.copyfileobj,
+        # to allow for padding and more control over the tar file writing.
+        self.tar._check("awx")
+
+        if fh is None and info.isreg() and info.size != 0:
+            raise ValueError("fileobj not provided for non zero-size regular file")
+
+        info = copy.copy(info)
+
+        buf = info.tobuf(self.tar.format, self.tar.encoding, self.tar.errors)
+        self.tar.fileobj.write(buf)
+        self.tar.offset += len(buf)
+        bufsize = self.tar.copybufsize
+        if fh is not None:
+            bufsize = bufsize or 16 * 1024
+
+            if info.size == 0:
+                return
+            if info.size is None:
+                shutil.copyfileobj(fh, self.tar.fileobj, bufsize)
+                return
+
+            blocks, remainder = divmod(info.size, bufsize)
+            for _ in range(blocks):
+                # Prevents "long reads" because it reads at max bufsize bytes at a time
+                buf = fh.read(bufsize)
+                if len(buf) < bufsize:
+                    # PATCH; instead of raising an exception, pad the data to the desired length
+                    buf += tarfile.NUL * (bufsize - len(buf))
+                self.tar.fileobj.write(buf)
+
+            if remainder != 0:
+                # Prevents "long reads" because it reads at max bufsize bytes at a time
+                buf = fh.read(remainder)
+                if len(buf) < remainder:
+                    # PATCH; instead of raising an exception, pad the data to the desired length
+                    buf += tarfile.NUL * (remainder - len(buf))
+                self.tar.fileobj.write(buf)
+
+            blocks, remainder = divmod(info.size, tarfile.BLOCKSIZE)
+            if remainder > 0:
+                self.tar.fileobj.write(tarfile.NUL * (tarfile.BLOCKSIZE - remainder))
+                blocks += 1
+            self.tar.offset += blocks * tarfile.BLOCKSIZE
+
+        self.tar.members.append(info)
 
     def close(self) -> None:
         """Closes the tar file."""
diff --git a/tests/test_outputs_tar.py b/tests/test_outputs_tar.py
index 81059bb2..49d00f86 100644
--- a/tests/test_outputs_tar.py
+++ b/tests/test_outputs_tar.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import io
 import tarfile
 from pathlib import Path
 from typing import TYPE_CHECKING
@@ -63,3 +64,77 @@ def test_tar_output_encrypt(mock_fs: VirtualFilesystem, public_key: bytes, tmp_p
 
     with tarfile.open(name=decrypted_path, mode="r") as tar_file:
         assert entry.open().read() == tar_file.extractfile(entry_name).read()
+
+
+def test_tar_output_race_condition_with_shrinking_file(tmp_path: Path, public_key: bytes) -> None:
+    class ShrinkingFile(io.BytesIO):
+        """
+        A file-like object that returns 5 bytes less than required.
+        Simulates a file on disk that has shrunk in between the time of
+        determining the size and actually reading the data.
+        """
+
+        def __init__(self, data: bytes):
+            super().__init__(data)
+
+        def read(self, size: int) -> bytes:
+            return super().read(size - 5)
+
+    content = b"some text"
+
+    content_padded = content[:-5] + tarfile.NUL * 5
+    file = ShrinkingFile(content)
+
+    tar_output = TarOutput(tmp_path / "race.tar", encrypt=True, public_key=public_key)
+    tar_output.write("file.log", file)
+    tar_output.close()
+    file.close()
+
+    encrypted_stream = EncryptedFile(tar_output.path.open("rb"), Path("tests/_data/private_key.pem"))
+    decrypted_path = tmp_path / "decrypted.tar"
+
+    # Direct streaming is not an option because tarfile needs seek when reading from encrypted files directly
+    Path(decrypted_path).write_bytes(encrypted_stream.read())
+
+    with tarfile.open(name=decrypted_path, mode="r") as tar_file:
+        member = tar_file.getmember("file.log")
+        extracted = tar_file.extractfile(member).read()
+        # The content should be padded with zeros to match the original size, despite the fact that the file shrunk
+        assert extracted == content_padded
+
+
+def test_tar_output_race_condition_with_growing_file(tmp_path: Path, public_key: bytes) -> None:
+    class GrowingFile(io.BytesIO):
+        """
+        A file-like object that returns 3 extra bytes.
+        Simulates a file on disk that has grown in between the time of
+        determining the size and actually reading the data.
+        """
+
+        def __init__(self, data: bytes):
+            super().__init__(data)
+
+        def read(self, size: int) -> bytes:
+            return super().read(size) + b"FOX"
+
+    content = b"some text"
+
+    file = GrowingFile(content)
+
+    tar_output = TarOutput(tmp_path / "race.tar", encrypt=True, public_key=public_key)
+    tar_output.write("file.log", file)
+    tar_output.close()
+    file.close()
+
+    encrypted_stream = EncryptedFile(tar_output.path.open("rb"), Path("tests/_data/private_key.pem"))
+    decrypted_path = tmp_path / "decrypted.tar"
+
+    # Direct streaming is not an option because tarfile needs seek when reading from encrypted files directly
+    Path(decrypted_path).write_bytes(encrypted_stream.read())
+
+    with tarfile.open(name=decrypted_path, mode="r") as tar_file:
+        member = tar_file.getmember("file.log")
+        extracted = tar_file.extractfile(member).read()
+        # The content should match the original content, without the extra bytes
+        # because the file was read with the original size
+        assert extracted == content