diff --git a/shared/middleware/files_api.rb b/shared/middleware/files_api.rb
index 6ad090f771de7..87a83f2426136 100644
--- a/shared/middleware/files_api.rb
+++ b/shared/middleware/files_api.rb
@@ -576,6 +576,7 @@ def files_put_file(encrypted_channel_id, filename, body)
     unescaped_filename = CGI.unescape(filename)
     unescaped_filename_downcased = unescaped_filename.downcase
     bad_request if unescaped_filename_downcased == FileBucket::MANIFEST_FILENAME
+    bad_request if unescaped_filename_downcased.length > FileBucket::MAXIMUM_FILENAME_LENGTH
 
     bucket = FileBucket.new
     manifest = get_manifest(bucket, encrypted_channel_id)
diff --git a/shared/middleware/helpers/file_bucket.rb b/shared/middleware/helpers/file_bucket.rb
index 757a00a2c0a93..f87c837526ff7 100644
--- a/shared/middleware/helpers/file_bucket.rb
+++ b/shared/middleware/helpers/file_bucket.rb
@@ -3,6 +3,7 @@
 #
 class FileBucket < BucketHelper
   MANIFEST_FILENAME = 'manifest.json'.freeze
+  MAXIMUM_FILENAME_LENGTH = 512
 
   def initialize
     super CDO.files_s3_bucket, CDO.files_s3_directory
diff --git a/shared/test/fixtures/vcr/files/rename_object_filename_too_long.yml b/shared/test/fixtures/vcr/files/rename_object_filename_too_long.yml
new file mode 100644
index 0000000000000..085f54494def9
--- /dev/null
+++ b/shared/test/fixtures/vcr/files/rename_object_filename_too_long.yml
@@ -0,0 +1,564 @@
+---
+http_interactions:
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/manifest.json
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 404
+      message: Not Found
+    headers:
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Date:
+      - Fri, 14 Sep 2018 00:26:14 GMT
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <Error><Code>NoSuchKey</Code><Message>The specified key does not exist.</Message><Key>files_test/1/1/manifest.json</Key><RequestId>504D13988B6EB8F6</RequestId><HostId>hqq77K0eRC/1HJjGM94e5Jb+w5JKEhXvT6ddRFP8BacCUEP9CNhU7EpZZrcCT2jPOpsBXuFU1Mo=</HostId></Error>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:14 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/?encoding-type=url&prefix=files_test/1/1/old_fileac0a7f8c2faac49775a6.html&versions
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:15 GMT
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <ListVersionsResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"><Name>cdo-v3-files</Name><Prefix>files_test/1/1/old_fileac0a7f8c2faac49775a6.html</Prefix><KeyMarker></KeyMarker><VersionIdMarker></VersionIdMarker><MaxKeys>1000</MaxKeys><EncodingType>url</EncodingType><IsTruncated>false</IsTruncated><DeleteMarker><Key>files_test/1/1/old_fileac0a7f8c2faac49775a6.html</Key><VersionId>XeE4zbyCWcdtFj9zz5BtdkLcVP8jc8aM</VersionId><IsLatest>true</IsLatest><LastModified>2018-09-14T00:14:23.000Z</LastModified><Owner><ID>cf6bd5437eaccbf2d79d5d40694e94c727ef59eb29caa52acbc32daffeb8e9e4</ID><DisplayName>site</DisplayName></Owner></DeleteMarker><Version><Key>files_test/1/1/old_fileac0a7f8c2faac49775a6.html</Key><VersionId>h0WFzSBtrtKvenikZaXW3_7Br7ZqZwKb</VersionId><IsLatest>false</IsLatest><LastModified>2018-09-14T00:14:21.000Z</LastModified><ETag>&quot;458b68094909507177f21dc1c238829d&quot;</ETag><Size>14</Size><Owner><ID>cf6bd5437eaccbf2d79d5d40694e94c727ef59eb29caa52acbc32daffeb8e9e4</ID><DisplayName>site</DisplayName></Owner><StorageClass>STANDARD</StorageClass></Version></ListVersionsResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:15 GMT
+- request:
+    method: post
+    uri: https://cdo-v3-files.s3.amazonaws.com/?delete
+    body:
+      encoding: UTF-8
+      string: |
+        <Delete xmlns="http://s3.amazonaws.com/doc/2006-03-01/">
+          <Object>
+            <Key>files_test/1/1/old_fileac0a7f8c2faac49775a6.html</Key>
+            <VersionId>h0WFzSBtrtKvenikZaXW3_7Br7ZqZwKb</VersionId>
+          </Object>
+          <Object>
+            <Key>files_test/1/1/old_fileac0a7f8c2faac49775a6.html</Key>
+            <VersionId>XeE4zbyCWcdtFj9zz5BtdkLcVP8jc8aM</VersionId>
+          </Object>
+          <Quiet>true</Quiet>
+        </Delete>
+    headers:
+      Expect:
+      - 100-continue
+      Content-Md5:
+      - lMt9TLBnKIbs5pPD4Lr0nA==
+      Content-Length:
+      - '383'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:16 GMT
+      Connection:
+      - close
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <DeleteResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"></DeleteResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:15 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/?encoding-type=url&prefix=files_test/1/1/old_fileac0a7f8c2faac49775a6.html&versions
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:16 GMT
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <ListVersionsResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"><Name>cdo-v3-files</Name><Prefix>files_test/1/1/old_fileac0a7f8c2faac49775a6.html</Prefix><KeyMarker></KeyMarker><VersionIdMarker></VersionIdMarker><MaxKeys>1000</MaxKeys><EncodingType>url</EncodingType><IsTruncated>false</IsTruncated></ListVersionsResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:15 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/?encoding-type=url&prefix=files_test/1/1/manifest.json&versions
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:17 GMT
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <ListVersionsResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"><Name>cdo-v3-files</Name><Prefix>files_test/1/1/manifest.json</Prefix><KeyMarker></KeyMarker><VersionIdMarker></VersionIdMarker><MaxKeys>1000</MaxKeys><EncodingType>url</EncodingType><IsTruncated>false</IsTruncated></ListVersionsResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:16 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/manifest.json
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 404
+      message: Not Found
+    headers:
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Date:
+      - Fri, 14 Sep 2018 00:26:15 GMT
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <Error><Code>NoSuchKey</Code><Message>The specified key does not exist.</Message><Key>files_test/1/1/manifest.json</Key><RequestId>C0499F195E516993</RequestId><HostId>OcrFO9qiRruGCavqnkn/reCeeHvqK+3sJdU1vXH1UAn1lEwY/G/kNgkThI/YDNKRoD0N19wIIEY=</HostId></Error>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:16 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/?encoding-type=url&prefix=files_test/1/1/
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:17 GMT
+      X-Amz-Bucket-Region:
+      - us-east-1
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <ListBucketResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"><Name>cdo-v3-files</Name><Prefix>files_test/1/1/</Prefix><Marker></Marker><MaxKeys>1000</MaxKeys><EncodingType>url</EncodingType><IsTruncated>false</IsTruncated></ListBucketResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:16 GMT
+- request:
+    method: put
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/old_fileac0a7f8c2faac49775a6.html
+    body:
+      encoding: ASCII-8BIT
+      string: fake-file-data
+    headers:
+      X-Amz-Meta-Abuse-Score:
+      - '0'
+      Expect:
+      - 100-continue
+      Content-Md5:
+      - RYtoCUkJUHF38h3BwjiCnQ==
+      Content-Length:
+      - '14'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:18 GMT
+      X-Amz-Version-Id:
+      - VUk3mTnPAGEVDx1XdZu0FRMc4lKeR_zl
+      Etag:
+      - '"458b68094909507177f21dc1c238829d"'
+      Content-Length:
+      - '0'
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: ''
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:17 GMT
+- request:
+    method: put
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/manifest.json
+    body:
+      encoding: UTF-8
+      string: '[{"filename":"old_fileac0a7f8c2faac49775a6.html","category":"text","size":14,"versionId":"VUk3mTnPAGEVDx1XdZu0FRMc4lKeR_zl","timestamp":"2018-09-13T17:26:17.195-07:00"}]'
+    headers:
+      X-Amz-Meta-Abuse-Score:
+      - '0'
+      Expect:
+      - 100-continue
+      Content-Md5:
+      - EDBgyU/DSDMh7U519WGRug==
+      Content-Length:
+      - '169'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:18 GMT
+      X-Amz-Version-Id:
+      - IyObkRYt1T4pyT9d..t1W7v4os95OQFp
+      Etag:
+      - '"103060c94fc3483321ed4e75f56191ba"'
+      Content-Length:
+      - '0'
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: ''
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:17 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/long_filename________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________.html
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 404
+      message: Not Found
+    headers:
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Date:
+      - Fri, 14 Sep 2018 00:26:17 GMT
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <Error><Code>NoSuchKey</Code><Message>The specified key does not exist.</Message><Key>files_test/1/1/long_filename________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________.html</Key><RequestId>DE215D49B9285792</RequestId><HostId>FPtaxnEbusX9xGLqXNDt3GsVgA2NZ/b2wPbdD2jisXk7bbMyMSc03PE6hVE0NovSFOPRkMi7JWQ=</HostId></Error>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:17 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/old_fileac0a7f8c2faac49775a6.html
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:19 GMT
+      Last-Modified:
+      - Fri, 14 Sep 2018 00:26:18 GMT
+      Etag:
+      - '"458b68094909507177f21dc1c238829d"'
+      X-Amz-Meta-Abuse-Score:
+      - '0'
+      X-Amz-Version-Id:
+      - VUk3mTnPAGEVDx1XdZu0FRMc4lKeR_zl
+      Accept-Ranges:
+      - bytes
+      Content-Type:
+      - ''
+      Content-Length:
+      - '14'
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: fake-file-data
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:18 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/manifest.json
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:19 GMT
+      Last-Modified:
+      - Fri, 14 Sep 2018 00:26:18 GMT
+      Etag:
+      - '"103060c94fc3483321ed4e75f56191ba"'
+      X-Amz-Meta-Abuse-Score:
+      - '0'
+      X-Amz-Version-Id:
+      - IyObkRYt1T4pyT9d..t1W7v4os95OQFp
+      Accept-Ranges:
+      - bytes
+      Content-Type:
+      - ''
+      Content-Length:
+      - '169'
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: '[{"filename":"old_fileac0a7f8c2faac49775a6.html","category":"text","size":14,"versionId":"VUk3mTnPAGEVDx1XdZu0FRMc4lKeR_zl","timestamp":"2018-09-13T17:26:17.195-07:00"}]'
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:18 GMT
+- request:
+    method: put
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/manifest.json
+    body:
+      encoding: UTF-8
+      string: "[]"
+    headers:
+      X-Amz-Meta-Abuse-Score:
+      - '0'
+      Expect:
+      - 100-continue
+      Content-Md5:
+      - 11FxOYiYfpMxmANj4kGJzg==
+      Content-Length:
+      - '2'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:19 GMT
+      X-Amz-Version-Id:
+      - ASNMdK39C.YS645GxfT9WF8v1n.BfUfN
+      Etag:
+      - '"d751713988987e9331980363e24189ce"'
+      Content-Length:
+      - '0'
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: ''
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:19 GMT
+- request:
+    method: delete
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/old_fileac0a7f8c2faac49775a6.html
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 204
+      message: No Content
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:20 GMT
+      X-Amz-Version-Id:
+      - oWKsjuSOYr3rlZlIcuWBkgggNFbaKwh1
+      X-Amz-Delete-Marker:
+      - 'true'
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: ''
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:19 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/?encoding-type=url&prefix=files_test/1/1/manifest.json&versions
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:20 GMT
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <ListVersionsResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"><Name>cdo-v3-files</Name><Prefix>files_test/1/1/manifest.json</Prefix><KeyMarker></KeyMarker><VersionIdMarker></VersionIdMarker><MaxKeys>1000</MaxKeys><EncodingType>url</EncodingType><IsTruncated>false</IsTruncated><Version><Key>files_test/1/1/manifest.json</Key><VersionId>ASNMdK39C.YS645GxfT9WF8v1n.BfUfN</VersionId><IsLatest>true</IsLatest><LastModified>2018-09-14T00:26:19.000Z</LastModified><ETag>&quot;d751713988987e9331980363e24189ce&quot;</ETag><Size>2</Size><Owner><ID>cf6bd5437eaccbf2d79d5d40694e94c727ef59eb29caa52acbc32daffeb8e9e4</ID><DisplayName>site</DisplayName></Owner><StorageClass>STANDARD</StorageClass></Version><Version><Key>files_test/1/1/manifest.json</Key><VersionId>IyObkRYt1T4pyT9d..t1W7v4os95OQFp</VersionId><IsLatest>false</IsLatest><LastModified>2018-09-14T00:26:18.000Z</LastModified><ETag>&quot;103060c94fc3483321ed4e75f56191ba&quot;</ETag><Size>169</Size><Owner><ID>cf6bd5437eaccbf2d79d5d40694e94c727ef59eb29caa52acbc32daffeb8e9e4</ID><DisplayName>site</DisplayName></Owner><StorageClass>STANDARD</StorageClass></Version></ListVersionsResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:19 GMT
+- request:
+    method: post
+    uri: https://cdo-v3-files.s3.amazonaws.com/?delete
+    body:
+      encoding: UTF-8
+      string: |
+        <Delete xmlns="http://s3.amazonaws.com/doc/2006-03-01/">
+          <Object>
+            <Key>files_test/1/1/manifest.json</Key>
+            <VersionId>ASNMdK39C.YS645GxfT9WF8v1n.BfUfN</VersionId>
+          </Object>
+          <Object>
+            <Key>files_test/1/1/manifest.json</Key>
+            <VersionId>IyObkRYt1T4pyT9d..t1W7v4os95OQFp</VersionId>
+          </Object>
+          <Quiet>true</Quiet>
+        </Delete>
+    headers:
+      Expect:
+      - 100-continue
+      Content-Md5:
+      - Vo5w2669bW4d3UsiVwdXCw==
+      Content-Length:
+      - '343'
+  response:
+    status:
+      code: 200
+      message: OK
+    headers:
+      Date:
+      - Fri, 14 Sep 2018 00:26:20 GMT
+      Connection:
+      - close
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <DeleteResult xmlns="http://s3.amazonaws.com/doc/2006-03-01/"></DeleteResult>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:20 GMT
+- request:
+    method: get
+    uri: https://cdo-v3-files.s3.amazonaws.com/files_test/1/1/manifest.json
+    body:
+      encoding: UTF-8
+      string: ''
+    headers:
+      Content-Length:
+      - '0'
+  response:
+    status:
+      code: 404
+      message: Not Found
+    headers:
+      Content-Type:
+      - application/xml
+      Transfer-Encoding:
+      - chunked
+      Date:
+      - Fri, 14 Sep 2018 00:26:19 GMT
+      Server:
+      - AmazonS3
+    body:
+      encoding: UTF-8
+      string: |-
+        <?xml version="1.0" encoding="UTF-8"?>
+        <Error><Code>NoSuchKey</Code><Message>The specified key does not exist.</Message><Key>files_test/1/1/manifest.json</Key><RequestId>04142AAD8D4791A6</RequestId><HostId>NycKPklMz0wPSO1qsRXVKQswCrkGe9H9STRMhPGoOY3iUIGFxqSI/24pVmfxKxBvl2XRWXGirgE=</HostId></Error>
+    http_version: 
+  recorded_at: Fri, 14 Sep 2018 00:26:20 GMT
+recorded_with: VCR 3.0.3
diff --git a/shared/test/test_files.rb b/shared/test/test_files.rb
index ced70e77e7ccf..b955c26cfe621 100644
--- a/shared/test/test_files.rb
+++ b/shared/test/test_files.rb
@@ -68,6 +68,28 @@ def test_rename_object
     delete_all_manifest_versions
   end
 
+  def test_rename_object_filename_too_long
+    file_data = 'fake-file-data'
+    old_filename = @api.randomize_filename 'old_file.html'
+    new_filename = "long_filename#{'_' * 512}.html"
+    delete_all_file_versions old_filename, URI.escape(old_filename)
+    delete_all_manifest_versions
+    post_file_data @api, old_filename, file_data, 'test/html'
+
+    @api.rename_object old_filename, new_filename
+    assert bad_request?
+    @api.get_object(new_filename)
+    assert not_found?
+    @api.get_object(old_filename)
+    assert successful?
+    assert_equal file_data, last_response.body
+
+    @api.delete_object(old_filename)
+    assert successful?
+
+    delete_all_manifest_versions
+  end
+
   def test_upload_files
     dog_image_filename = @api.randomize_filename('dog.png')
     dog_image_body = 'stub-dog-contents'