Since I'm currently experiencing the issue, I've been able to get some better 
data. I've managed to reproduce it in 8.2.0.2 CS, which suggests it's not 
https://github.com/racket/racket/issues/3804.

Restarting twice DrRacket hasn't helped, nor has resetting my wifi connection.

After connecting via a browser, I notice a lot of the following in the log that 
seem to correlate with my attempts in the browser:
> [-|2021-09-18T19:37:45] handin: unknown protocol: #"GET / HTTP/1.1"
> ...
> [-|2021-09-18T19:37:53] ERROR: ssl-accept/enable-break: accept failed 
> (error:1408F09C:SSL routines:ssl3_get_record:http request)

As expected, nothing seem to correlate with my attempts to connect from the 
handin plugin.

This makes me suspect the server, but I can't reconcile that with why there's 
nothing in the logs.

--
William J. Bowman

On Sat, Sep 18, 2021 at 06:59:43PM -0700, 'William J. Bowman' via Racket Users 
wrote:
> I just tried this, but I can't seem to connect.
>   http://cs110.students.cs.ubc.ca:7979/
> gives "connection reset", and 
>   https://cs110.students.cs.ubc.ca:7979/
> gives "secure connection failed".
> 
> There's no prompt to accept the certificate (which I wouldn't expect, because 
> we're using a CA signed certificate through Let's Encrypt, not a self-signed 
> certificate).
> 
> I'm currently experiencing the problem on my own client. I'm not sure if 
> that's related; I also couldn't connect from my phone.
> 
> --
> William J. Bowman
> 
> On Sat, Sep 18, 2021 at 09:24:05PM -0400, Sam Tobin-Hochstadt wrote:
> > Have you tried visiting the server with a browser? That should work,
> > although you'll have to accept the certificate. It might also indicate some
> > aspect of the behavior.
> > 
> > Sam
> > 
> > On Sat, Sep 18, 2021, 7:13 PM 'William J. Bowman' via Racket Users <
> > [email protected]> wrote:
> > 
> > > I need some help debugging an issue with the handin package. The handin
> > > plugin (client) displays “Making secure connection to <handin server> …”,
> > > and simply hangs. Closing the dialog and trying again never resolves the
> > > issue.
> > >
> > > The only method that seems to resolve the issue, although inconsistently,
> > > is restarting DrRacket, opening a new file, and trying to submit that new
> > > file. This sometimes, but not always, enables the client to connect. Once
> > > it does connect, the issue doesn't seem to recur for some time. The client
> > > can make multiple successful submissions, at least until the end of 
> > > lecture
> > > (maybe related to the next time they disconnect/reconnect to the 
> > > internet).
> > >
> > > We running Racket 7.8 on the server and 8.1 BC on the clients. We've seen
> > > the issue occur on many operating system---old and new versions of macOS,
> > > Windows 10, and at one report on Linux.
> > >
> > > I can't just upgrade the clients to 8.2, since there's a bug in 8.2 that
> > > affects rendering inexact numbers in BSL, so I really want some confidence
> > > about what the issue is before I start upgrading versions.
> > >
> > > Anecdotally, the problem seems more common this semester compared to the
> > > previous semester, and we upgraded the clients to 8.1 this semester,
> > > suggesting the clients are at fault.
> > >
> > > When this problem occurs, there is nothing in the log on the handin
> > > server, suggesting the client did not even manage to initiate the
> > > connection to the server. In particular, the server never seems to make it
> > > to this log line:
> > >
> > > https://github.com/racket/handin/blob/ac08937cc6b1eca8abe3d4d4df59876f95cbea17/handin-server/main.rkt#L679
> > > This is one the earliest log lines and before pretty much anything
> > > happens, so we're *PRETTY SURE* the client is blocking.
> > >
> > > Right now, my best guess is that we might be affected by this bug, which
> > > causes SSL ports to block incorrectly:
> > >   https://github.com/racket/racket/issues/3804
> > >
> > > If so, it would probably be in the client, unless `(ssl-addresses r)` can
> > > block in the same way on the server, since otherwise the above log line
> > > would execute.
> > >
> > > However, if it is the client, I don't have any explanation about why
> > > restarting DrRacket would workaround the bug, or why it sometimes doesn't
> > > work.
> > >
> > > I'd appreciate any help.
> > >
> > > --
> > > William J. Bowman
> > >
> > > --
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> > > https://groups.google.com/d/msgid/racket-users/YUZyWlsY9CdCDyPu%40williamjbowman.com
> > > .
> > >
> 
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