diff --git a/src/sentry/models/file.py b/src/sentry/models/file.py
index 3f4860b6f7c01c..3c3e9252f65e63 100644
--- a/src/sentry/models/file.py
+++ b/src/sentry/models/file.py
@@ -58,7 +58,7 @@ def enum(**named_values):
 def _get_size_and_checksum(fileobj):
     size = 0
     checksum = sha1()
-    while 1:
+    while True:
         chunk = fileobj.read(65536)
         if not chunk:
             break
@@ -134,7 +134,7 @@ def from_files(cls, files, organization=None):
 
         def _upload_and_pend_chunk(fileobj, size, checksum, lock):
             blob = cls(size=size, checksum=checksum)
-            blob.path = cls.generate_unique_path(blob.timestamp)
+            blob.path = cls.generate_unique_path()
             storage = get_storage()
             storage.save(blob.path, fileobj)
             blobs_to_save.append((blob, lock))
@@ -156,7 +156,7 @@ def _save_blob(blob):
             _ensure_blob_owned(blob)
 
         def _flush_blobs():
-            while 1:
+            while True:
                 try:
                     blob, lock = blobs_to_save.pop()
                 except IndexError:
@@ -229,7 +229,7 @@ def from_file(cls, fileobj):
                 return existing
 
             blob = cls(size=size, checksum=checksum)
-            blob.path = cls.generate_unique_path(blob.timestamp)
+            blob.path = cls.generate_unique_path()
             storage = get_storage()
             storage.save(blob.path, fileobj)
             blob.save()
@@ -238,9 +238,11 @@ def from_file(cls, fileobj):
         return blob
 
     @classmethod
-    def generate_unique_path(cls, timestamp):
-        pieces = [six.text_type(x) for x in divmod(int(timestamp.strftime('%s')), ONE_DAY)]
-        pieces.append(uuid4().hex)
+    def generate_unique_path(cls):
+        # We intentionally do not use checksums as path names to avoid concurrency issues
+        # when we attempt concurrent uploads for any reason.
+        uuid_hex = uuid4().hex
+        pieces = [uuid_hex[:2], uuid_hex[2:6], uuid_hex[6:]]
         return u'/'.join(pieces)
 
     def delete(self, *args, **kwargs):
diff --git a/tests/sentry/models/test_file.py b/tests/sentry/models/test_file.py
index d26b7981be8d09..f7bf4d51a60e52 100644
--- a/tests/sentry/models/test_file.py
+++ b/tests/sentry/models/test_file.py
@@ -24,6 +24,18 @@ def test_from_file(self):
         assert my_file1.checksum == my_file2.checksum
         assert my_file1.path == my_file2.path
 
+    def test_generate_unique_path(self):
+        path = FileBlob.generate_unique_path()
+        assert path
+
+        parts = path.split('/')
+        assert len(parts) == 3
+        assert map(len, parts) == [2, 4, 26]
+
+        # Check uniqueness
+        path2 = FileBlob.generate_unique_path()
+        assert path != path2
+
 
 class FileTest(TestCase):
     def test_file_handling(self):