The web engine is probably on the mail server.  IIS wouldn't be relevant.
I'd at least have an NGINX proxy to secure it from the outside work, then
the only unencrypted communication is between two adjacent severs.

The HTTPS warning you're talking about is a self signed one.  It'd be like
the cop telling you he's not a cop.

The mail server doesn't speak HTTPS which is your issue.  More than likely
your address bar had https instead of http.  Safe browsing would give you a
different error.

On Wed, Nov 4, 2026 at 11:02 AM Ken Hohhof <[email protected]> wrote:

> This is a mailserver running the old Ipswitch iMail software, acquired by
> Progress Software then EOL’d.  Serves a handful of mostly former customers
> from the dialup and DSL days.  I’ve spent a decade trying to push them to
> Gmail.
>
>
>
> There are no options for HTTPS in the iMail menus.  A Google search tells
> me it might be possible to configure directly in IIS and install or
> generate a certificate.  I’m scared to mess with it, probably will be shut
> down soon anyway.
>
>
>
> I work on network devices all the time that don’t support HTTPS and just
> get a warning from the browser though.  I was surprised it acted like the
> site was unreachable.  If I disable Google Safe Browsing it goes away.
> Very strange.
>
>
>
> *From:* AF <[email protected]> *On Behalf Of *Josh Luthman
> *Sent:* Wednesday, November 4, 2026 9:41 AM
> *To:* AnimalFarm Microwave Users Group <[email protected]>
> *Subject:* Re: [AFMUG] site can't be reached using Chrome
>
>
>
> Chrome really wants to use https.  If you just type that with no protocol,
> it will attempt https and then stop.
>
>
>
> That site works with http.
>
>
>
> It's scary that you're doing user/pass over http.
>
>
>
> On Sun, Nov 1, 2026 at 11:30 AM Ken Hohhof <[email protected]> wrote:
>
> I’m getting “site can’t be reached” for webmail.kwom.com using Chrome (or
> Brave).  Works fine with Edge or Firefox.  Not a security, privacy or
> certificate warning, it’s as if the site is offline.
>
>
>
> Any ideas?  Tried a Google search and none of the suggestions helped.
>
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