diff --git a/win_toolchain/get_toolchain_if_necessary.py b/win_toolchain/get_toolchain_if_necessary.py
index fb8a87adb..a5956055e 100755
--- a/win_toolchain/get_toolchain_if_necessary.py
+++ b/win_toolchain/get_toolchain_if_necessary.py
@@ -183,8 +183,12 @@ def CalculateHash(root, expected_hash):
       digest.update(f.read())
 
   # Save the timestamp file if the calculated hash is the expected one.
-  if digest.hexdigest() == expected_hash:
+  # The expected hash may be shorter, to reduce path lengths, in which case just
+  # compare that many characters.
+  if expected_hash and digest.hexdigest()[:len(expected_hash)] == expected_hash:
     SaveTimestampsAndHash(root, digest.hexdigest())
+    # Return the (potentially truncated) expected_hash.
+    return expected_hash
   return digest.hexdigest()
 
 
diff --git a/win_toolchain/package_from_installed.py b/win_toolchain/package_from_installed.py
index 6794f955b..d3c3f23f4 100644
--- a/win_toolchain/package_from_installed.py
+++ b/win_toolchain/package_from_installed.py
@@ -424,6 +424,10 @@ def RenameToSha1(output):
     zf.extractall(rel_dir)
   print('Hashing...')
   sha1 = get_toolchain_if_necessary.CalculateHash(rel_dir, None)
+  # Shorten from forty characters to ten. This is still enough to avoid
+  # collisions, while being less unwieldy and reducing the risk of MAX_PATH
+  # failures.
+  sha1 = sha1[:10]
   os.chdir(old_dir)
   shutil.rmtree(tempdir)
   final_name = sha1 + '.zip'