Disconnects During Synchonization

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OpFor
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Disconnects During Synchonization

I have WinSCP running on multiple clients accessing the same server (Windows Server 2008 R2). The problem I'm having is that during synchronization, whether uploading or comparing, the connection seemingly randomly drops. Here are some logs when trying to upload synchronized changes.

WinSCP log:
> 2022-08-31 21:31:52.213 MKD FileHandlers
< 2022-08-31 21:31:52.213 257 "FileHandlers" directory created.
> 2022-08-31 21:31:52.213 CWD /REDACTED/Test/plugins/FileHandlers
< 2022-08-31 21:31:52.229 250 CWD command successful.
> 2022-08-31 21:31:52.229 MKD OBJReader
< 2022-08-31 21:31:52.229 257 "OBJReader" directory created.
> 2022-08-31 21:31:52.229 CWD /REDACTED/Test/plugins/FileHandlers/OBJReader
< 2022-08-31 21:31:52.229 250 CWD command successful.
> 2022-08-31 21:31:52.229 PWD
. 2022-08-31 21:31:52.229 Disconnected from server
. 2022-08-31 21:31:52.229 Copying files to remote side failed.
. 2022-08-31 21:31:52.229 Connection was lost, asking what to do.
. 2022-08-31 21:31:52.229 Asking user:
. 2022-08-31 21:31:52.229 **Lost connection.** ("Disconnected from server","Copying files to remote side failed.")
. 2022-08-31 21:31:54.685 Answer: Abort
* 2022-08-31 21:31:54.805 (EFatal) **Lost connection.**
* 2022-08-31 21:31:54.805 Disconnected from server
* 2022-08-31 21:31:54.805 Copying files to remote side failed.
* 2022-08-31 21:31:54.805 Copying files to remote side failed. 
Server side log at the same time period. The server logs in UTC, but it's interesting to me they are off by approximately 20 seconds. Is that significant at all?
2022-09-01 04:31:39 10.0.0.1 50232 - 10.0.0.5 21 MKD FileHandlers 257 0 0 /REDACTED/Test/plugins/FileHandlers -
2022-09-01 04:31:39 10.0.0.1 50232 - 10.0.0.5 21 CWD /REDACTED/Test/plugins/FileHandlers 250 0 0 /REDACTED/Test/plugins/FileHandlers -
2022-09-01 04:31:39 10.0.0.1 50232 - 10.0.0.5 21 MKD OBJReader 257 0 0 /REDACTED/Test/plugins/FileHandlers/OBJReader -
2022-09-01 04:31:39 10.0.0.1 50232 - 10.0.0.5 21 CWD /REDACTED/Test/plugins/FileHandlers/OBJReader 250 0 0 /REDACTED/Test/plugins/FileHandlers/OBJReader -
2022-09-01 04:31:39 10.0.0.1 50232 - 10.0.0.5 21 ControlChannelClosed - - 64 0 - -
It doesn't look like anything significant is happening to end the connection. The only thing odd I see is the timestamps. At timestamp 2022-08-31 21:31:52.229 you can see when WinSCP requests changing the working directory at the server. At timestamp 2022-09-01 04:31:39 the server changes the directory. After that at timestamp 2022-08-31 21:31:52.229 WinSCP requests to know what directory it's in (PWD), but then it just... Fails. The server shows the control channel closed, and WinSCP says it's disconnected from the server. The end.

Does anyone have any ideas what's going on here?

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