I need to put a message about this on our signup page (which means I need to figure out how to do that), but I thought I'd mention it:
Microsoft's servers almost always reject our mail, and there is no clear process for resolving this. We recently went to the trouble of setting up DMARC (which I still find baffling), but apparently they're still blocking us. I set up SPF years ago, too.
Microsoft's email services include hotmail.com, outlook.com and apparently even some university systems (an email recently sent to uga.edu showed that it was handled by a couple of subdomains of prod.outlook.com -- claiming that had been delivered, but probably to a spam folder).
(Also, just... don't use Microsoft products if you can avoid it.)
@woozle For my information, which domain is this? I know that M$ and the Big G both have severe penalties on emails send from smaller domains, so it's useful to know. For example, sending from an *.xyz domain is really, really hard.
And ... good luck.
TootCat sends emails from toot.cat (which is only available from a few registrars, hence not widely popular with spammers), but I have the same problem sending from .com and .org domains.
@woozle I've heard this a lot, and have ... I think ... experienced it from my own domain, solipsys.co.uk ... sometimes emails just disappear.
@woozle this is an issue with all email addresses hosted by MS Exchange Online in addition to Microsoft's own domains, so not just certain universities but also countless businesses and other institutions that have outsourced their infrastructure to Microsift
They are the WORST...even worse than Google. Besides strictly enforcing SPF and DMARC they are also strict about having exacting PTR entries, using the proper TLS configuration, and appear to have some sort of block list of IP addresses that they deem to be in "dynamic IP blocks"
The process of making an email server worthy would certainly give Kafka inspiration and is certainly far in excess of what is required for spam control
@woozle also I see the typo at the end of the first sentence but leaving it because it is the most appropriate typo ever
@rob @woozle be aware the effect is not permanent; you may be arbitrarily blocked again by their automated systems as the rules and algorithms evolve. But yeah you can buy yourself a few years of trouble free time.
MSFT doesn't use public block lists from what I can tell. Instead they maintain their own. Ultimately the most reliable solutiom is to tell your contacts to explicitly add your email addresses to their own contacts, as that will override policies that dump your messages right into the spam folder (it is easier to make your emails not bounce but less so to keep them out of spam folders)
I'm kinda more inclined to not waste the time, and just say that if Microsoft wants to defederate from the emailverse, let them -- just make sure everyone understands that this is a thing.
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