Sorry it took me a while to be able to repeat this. Here are the verbose logs.
Phone
2017/02/18 21:31:28.709 (96 MB) (2973771) I PMKCameraUploadEngine.m:1877 | Asset IMG_6741.MOV is downloading data (100%). 2017/02/18 21:31:28.896 (96 MB) (2973771) I PMKAssetController.m:279 | Video export progress: 0.993535 2017/02/18 21:31:28.997 (96 MB) (2973771) I PMKAssetController.m:279 | Video export progress: 0.9945368 2017/02/18 21:31:29.098 (96 MB) (2973771) I PMKAssetController.m:279 | Video export progress: 0.9955464 2017/02/18 21:31:29.196 (96 MB) (2973771) I PMKAssetController.m:279 | Video export progress: 0.9965483 2017/02/18 21:31:29.312 (96 MB) (2973771) I PMKAssetController.m:279 | Video export progress: 0.997721 2017/02/18 21:31:29.511 (96 MB) (2973771) I PMKAssetController.m:279 | Video export progress: 0.9997247 2017/02/18 21:31:30.170 (96 MB) (2973820) I PMKAssetController.m:304 | Video export completed successfully. 2017/02/18 21:31:30.205 (96 MB) (2973822) I PMKCameraUploadEngine.m:1675 | Created data transfer task to check partial upload for IMG_6741.MOV 2017/02/18 21:31:30.205 (96 MB) (2973822) I PMKCameraUploadEngine.m:2009 | Ending background task. 2017/02/18 21:31:30.331 (96 MB) (2973771) D PMKDataTransferManager.m:1159 | Handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> (1 tasks) 2017/02/18 21:31:30.396 (96 MB) (2973771) D PMKDataTransferManager.m:445 | Finished handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> 2017/02/18 21:31:30.964 (96 MB) (2973771) D PMKDataTransferManager.m:1159 | Handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> (1 tasks) 2017/02/18 21:31:31.010 (96 MB) (2973771) D PMKDataTransferManager.m:445 | Finished handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> 2017/02/18 21:31:31.017 (96 MB) (2974697) I PMKCameraUploadEngine.m:1224 | Beginning background task. 2017/02/18 21:31:31.020 (96 MB) (2974697) I PMKCameraUploadEngine.m:2038 | Starting background timer with time: 39.92187087499769 2017/02/18 21:31:31.020 (96 MB) (2974697) I PMKCameraUploadEngine.m:2436 | Neither asset nor partial upload were found. Uploading from beginning. 2017/02/18 21:31:31.188 (96 MB) (2974475) I PMKCameraUploadEngine.m:1680 | Created data transfer task to upload IMG_6741.MOV 2017/02/18 21:31:31.188 (96 MB) (2974475) I PMKCameraUploadEngine.m:2009 | Ending background task. 2017/02/18 21:35:31.011 (96 MB) (2973771) D PMKDataTransferManager.m:1159 | Handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> (1 tasks) 2017/02/18 21:35:31.034 (96 MB) (2975578) D PMKNetworkTask.m:192 | SERVER (1ecfa8366c0e30e4c9351c98d3e42ae07e0a9c1c): GET /:/timeline?bufferedTime=0&duration=1922153&key=%2Flibrary%2Fmetadata%2F674&location=lan&playQueueItemID=775244&ratingKey=674&state=paused&time=0&X-Plex-Device-Name=XXXXXXXXXX 2017/02/18 21:35:31.096 (96 MB) (2973771) D PMKDataTransferManager.m:445 | Finished handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> 2017/02/18 21:35:53.317 (96 MB) (2973771) D PMKDataTransferManager.m:1159 | Handling background URL session events in <PMKDataTransferManager:0x174157760 name=CameraUpload> (1 tasks) 2017/02/18 21:35:53.365 (96 MB) (2975656) I PMKCameraUploadEngine.m:1224 | Beginning background task. 2017/02/18 21:35:53.369 (96 MB) (2975656) I PMKCameraUploadEngine.m:2038 | Starting background timer with time: 29.92760083335452 2017/02/18 21:35:53.369 (96 MB) (2975656) I PMKCameraUploadEngine.m:2485 | Something went wrong. Starting process over. 2017/02/18 21:35:53.369 (96 MB) (2975656) I PMKCameraUploadEngine.m:1771 | Ending upload. 2017/02/18 21:35:53.370 (96 MB) (2975656) I PMKCameraUploadEngine.m:1797 | In the middle of the upload process, attempting to finish up. 2017/02/18 21:35:53.370 (96 MB) (2975656) I PMKCameraUploadEngine.m:1801 | No more tasks, all done. 2017/02/18 21:35:53.370 (96 MB) (2975656) I PMKCameraUploadEngine.m:1832 | Upload ended.
Server
Feb 18, 2017 21:47:24.529 [1064] DEBUG - Request: [192.168.1.YYY:53969 (Subnet)] POST /library/metadata?createdAt=1484404429&filename=IMG_6741.MOV&locationID=10§ionID=5&subdirectory=XXXXXXXXXX&type=12 (6 live) TLS GZIP Signed-in Token (antgiant) Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Host => 192.168.1.XXX:32400 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * User-Agent => PlexMobile/4.7 (iPhone; iOS 10.2.1; Scale/3.00) Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Device-Screen-Density => 3 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Supported-Commands => abort,changeQuality Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Device => iPhone Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Platform => iOS Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Sync-Version => 2 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Token => xxxxxxxxxxxxxxxxxxxx Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Username => antgiant Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Provides => client,controller,sync-target,player,pubsub-player Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Version => 4.7 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Model => 8,2 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Content-Length => 0 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Product => Plex for iOS Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Connection => keep-alive Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Client-Identifier => 8A68175F-F1A7-4D06-B178-ED147687840D Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Accept-Language => en-US;q=1 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Device-Screen-Resolution => 1242x2208 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Device-Vendor => Apple Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Platform-Version => 10.2.1 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Accept => text/xml,application/xml Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Content-Type => application/octet-stream Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Accept-Encoding => gzip, deflate Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Http-Pipeline => infinite Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * Content-Range => bytes */5767835492 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * X-Plex-Device-Name => XXXXXXXXXX Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * createdAt => 1484404429 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * filename => IMG_6741.MOV Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * locationID => 10 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * sectionID => 5 Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * subdirectory => XXXXXXXXXX Feb 18, 2017 21:47:24.529 [1064] VERBOSE - * type => 12 Feb 18, 2017 21:47:24.900 [1064] WARN - SLOW QUERY: It took 375.000000 ms to retrieve 0 items. Feb 18, 2017 21:47:24.900 [8776] DEBUG - Completed: [192.168.1.YYY:53969] 404 POST /library/metadata?createdAt=1484404429&filename=IMG_6741.MOV&locationID=10§ionID=5&subdirectory=XXXXXXXXXX&type=12 (6 live) TLS GZIP 381ms 379 bytes Feb 18, 2017 21:47:25.064 [8776] DEBUG - Auth: We found auth token (xxxxxxxxxxxxxxxxxxxx), enabling token-based authentication. Feb 18, 2017 21:47:25.064 [8776] DEBUG - Auth: authenticated user 1 as antgiant Feb 18, 2017 21:47:25.064 [8776] DEBUG - Auth: Came in with a super-token, authorization succeeded. Feb 18, 2017 21:47:25.064 [8776] ERROR - Exception parsing request: bad lexical cast: source type value could not be interpreted as target Feb 18, 2017 21:47:25.064 [8776] DEBUG - Request: [192.168.1.YYY:53969 (Subnet)] POST /library/metadata?createdAt=1484404429&filename=IMG_6741.MOV&locationID=10§ionID=5&subdirectory=XXXXXXXXXX&type=12 (6 live) TLS GZIP Signed-in Token (antgiant) Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * Host => 192.168.1.XXX:32400 Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * User-Agent => PlexMobile/4.7 (iPhone; iOS 10.2.1; Scale/3.00) Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * X-Plex-Device-Screen-Density => 3 Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * X-Plex-Supported-Commands => abort,changeQuality Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * X-Plex-Device => iPhone Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * X-Plex-Platform => iOS Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * X-Plex-Sync-Version => 2 Feb 18, 2017 21:47:25.064 [8776] VERBOSE - * X-Plex-Token => xxxxxxxxxxxxxxxxxxxx Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Username => antgiant Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Provides => client,controller,sync-target,player,pubsub-player Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Version => 4.7 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Model => 8,2 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * Content-Length => 5767835492 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Product => Plex for iOS Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * Connection => keep-alive Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Client-Identifier => 8A68175F-F1A7-4D06-B178-ED147687840D Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * Accept-Language => en-US;q=1 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Device-Screen-Resolution => 1242x2208 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Device-Vendor => Apple Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Platform-Version => 10.2.1 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * Accept => text/xml,application/xml Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * Content-Type => application/octet-stream Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * Accept-Encoding => gzip, deflate Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Http-Pipeline => infinite Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * X-Plex-Device-Name => XXXXXXXXXX Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * createdAt => 1484404429 Feb 18, 2017 21:47:25.065 [8776] VERBOSE - * filename => IMG_6741.MOV Feb 18, 2017 21:47:25.066 [8776] VERBOSE - * locationID => 10 Feb 18, 2017 21:47:25.066 [8776] VERBOSE - * sectionID => 5 Feb 18, 2017 21:47:25.066 [8776] VERBOSE - * subdirectory => XXXXXXXXXX Feb 18, 2017 21:47:25.066 [8776] VERBOSE - * type => 12 Feb 18, 2017 21:47:25.067 [8780] DEBUG - Completed: [192.168.1.YYY:53969] 500 POST /library/metadata?createdAt=1484404429&filename=IMG_6741.MOV&locationID=10§ionID=5&subdirectory=XXXXXXXXXX&type=12 (6 live) TLS GZIP 1ms 357 bytes (pipelined: 2) Feb 18, 2017 21:47:25.068 [8780] DEBUG - Request: [192.168.1.YYY:53969 (WAN)] (6 live) TLS Signed-in Feb 18, 2017 21:47:25.068 [8780] ERROR - Error parsing HTTP request: Feb 18, 2017 21:47:25.068 [8776] DEBUG - Completed: [192.168.1.YYY:53969] 400 (6 live) TLS 0ms 246 bytes (pipelined: 3) Feb 18, 2017 21:47:25.068 [8780] DEBUG - Request: [192.168.1.YYY:53969 (WAN)] (6 live) TLS Signed-in Feb 18, 2017 21:47:25.068 [8780] ERROR - Error parsing HTTP request: ݔV鐍 Feb 18, 2017 21:47:25.068 [8776] DEBUG - Completed: [192.168.1.YYY:53969] 400 (6 live) TLS 0ms 246 bytes (pipelined: 4) Feb 18, 2017 21:47:25.068 [8780] DEBUG - Request: [192.168.1.YYY:53969 (WAN)] (6 live) TLS Signed-in Feb 18, 2017 21:47:25.068 [8780] ERROR - Error parsing HTTP request: e��ǂ햍 *࠲G: