WatchOS5 - "Could not load file-transfer-result" of WCSessionFileTransfer

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I'm trying to send 2 files to my Apple Watch app. It worked initially, but now I'm getting 2 errors printed in the console.

WCSession.default.transferFile(fileURL1, metadata: ["name":"first"])
WCSession.default.transferFile(fileURL2, metadata: ["name":"second")

Who is printing the error - is it my the test app on the iPhone?

Can I transfer 2 files in sequence, or are there limitations - do I need to wait for the first transfer to complete?

2018-11-18 11:05:53.010374-0500 SimpleWatchConnectivity[836:23347] [WC] -[WCFileStorage enumerateFileTransferResultsWithBlock:] could not load file data at path /var/mobile/Containers/Data/Application/C07047D9-87F7-4CBD-AE79-AAE26D93A400/Library/Application Support/com.apple.watchconnectivity/46CAD076-37A8-4B60-A93E-F0F21F457593/FileTransfers/D9E589D8-E21B-4A34-9A29-8D6B53E997D5/file-transfer-result

The documentation makes it seem like the files are enqueued, so I'm not sure as to what is causing the error:

/** The system will enqueue the file and transfer it to the counterpart app at an opportune time. The transfer of a file will continue after the sending app has exited. The counterpart app will receive a delegate callback on next launch if the file has successfully arrived. The metadata dictionary can only accept the property list types. */

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