Jayson Smith writes:

 > Is AOL known to silently discard mail they think is spam for some
 > reason?

I hope someone with actual experience will speak up, but my take is
that it's entirely possible.  (Footnotes are of historical interest,
but not directly relevant to solutions.)

The last time I had any insight into AOL was 2014, during the DMARC
development process.  The freemail providers lobbied to make their use
case eligible.[1]  Gmail didn't have an issue AFAIK, but both AOL and
Yahoo! were groaning from a mind-boggling flood of spam.  Gmail and
Yahoo! techs were very competent and helpful, and contributed a lot of
useful statistics and protocol ideas.  OTOH, the AOL representatives
clearly were dramatically under-resourced, and basically just pleading
for relief.

AOL was later acquired by Yahoo, which is now 90% owned by private
equity (ie, may be presumed completely unethical) and 10% by Verizon
(one of the most irresponsible ISPs).  I really doubt they invest in
best-practice email services :-(.  On the other hand, the extremely
competent tech from Yahoo is still there, managing all Yahoo/AOL email
services (AFAIK that means all freemail services provided by Verizon).
*sigh* *I* doooon't knooow... :-(

 > I replied to her message from the same server and she did receive
 > that reply, so they haven't outright blocked my IP or
 > something. Even if I could contact someone who knows what they're
 > doing at AOL, there are no error logs for me to show.

The big freemail providers are deliberately opaque about their
operations, so the following is generic advice -- I don't have
evidence that it will help.  But it's good advice! ;-)

First, you should check that your DNS records for DKIM and SPF are
up-to-date, and outgoing mail is being signed.  If you haven't done
this recently, you should do it anyway.  Over the years, stuff
happens, as they say. :-)

"Friends don't let friends use AOL."  I understand the pain of moving
your email to a new address, so I completely respect anyone's decision
to stick to their current one.  That's the easiest solution from your
point of view, so I mention it.  Gmail has historically been the
easiest of the big (opaque) providers to work with because they
conform to current best practices and don't negotiate anything else. :-รพ

The third suggestion is most burdensome for you: set up ARC
processing.  The Authenticated Received Chain protocol creates a chain
of custody, where each domain that alters the message in ways that
invalidate signatures testifies that in the received message the
sending IP was an authorized sender for the domain and/or the DKIM
signature validated.  This is good enough for most recipients, so it
should help with AOL if broken DKIM signatures or failed SPF
authorization are the problem.  I trust the OpenArc implementation
https://github.com/trusteddomainproject/OpenARC because I've worked
with Murray Kucherawy since the 2014 DMARC travesty.  I'm pretty sure
it's not so difficult on a single host, but if you're working with an
email provider with a complex MX system, they may balk.  (Of course
you may already have ARC if you're working with a major hosting
service.)

I'm not in a position to use ARC on my own host and have never needed
it, but I'll help as much as I can if you have problems with setup.
Mark will be back online in mid-September, I think he has some
experience.

HTH

Regards,
Steve

Footnotes: 
[1]  The original idea of DMARC was to protect "transactional mail
flows", ie, sensitive direct business mail such as conversations
between a bank and an account holder.  Freemail providers were out of
scope, because of mailing lists and other such usage.  Then in
2013-2014 there was a huge increase in spam flows of the particularly
pernicious "referred by a friend" kind based on theft of huge numbers
of contact lists from Yahoo and AOL.  The big 3 freemail providers
(with Gmail) got references to transactional flows purged from the
drafts, and in April 2014, Yahoo and AOL proceeded to protect their
"From" domain with p=reject.  Yahoo's representative claimed that
several tests showed that this would stop literally millions of spam
mails per *minute* during spam campaigns.  This is not inconceivable,
given that there were already botnets with millions of bots at that
time: multicast a spam to 100,000 waiting bots each with a list of 10
victims, there's your million in well under 1 minute.

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