Jayson,

The top blog post on this site is currently on the topic of getting Gmail and 
others to accept self-hosted email:

https://infosec.engineering

Looks like Jerry uses Mailgun.

Michael Reeder
mich...@hygeiacounseling.com
Baltimore, MD

On April 14, 2024 11:48:20 AM EDT, Michael Reeder -- Hygeia MS 
<mich...@securemail.hygeiacounseling.com> wrote:
>Jayson,
>
>I'm not sure I'm fully knowledgeable enough in this matter to help, but 
>maybe...
>
>For my Mastodon VPS I use sendpulse.com as the outgoing SMTP server.  They 
>have a surprisingly high threshold of free outbound SMTP messages they allow 
>per month before asking you for a paid plan.  So far, I have had no problem 
>with blocked messages, so you might try them?
>
>FYI -- This is a company based in Ukraine with their servers in Germany, so 
>not sure what happens if Russia makes further strides in the war.
>
>-- Michael
>
>*Michael Reeder, LCPC
>*
>*Hygeia Counseling Services : Baltimore / Mt. Washington Village location*
>*410-871-TALK / michael(at)hygeiacounseling.com*
>
>
>On 3/16/2024 11:10 AM, Jayson Smith wrote:
>> Hi,
>> 
>> What I mean is that I'd love to find a good, reliable smarthost I can direct 
>> my SMTP server on my VPS to use. I've heard knowledgeable friends say over 
>> and over and over again, "Anyone who runs their own Email server is just 
>> asking for trouble, it's not worth it any more." The real problem I'm seeing 
>> is that seemingly within the last few years, at least some VPS providers 
>> (Linode and Digital Ocean for sure) have started getting entire IP ranges 
>> put on blocklists. My first experience of being put on UCEPROTECT level 3 
>> was on January 20, 2021, and a few weeks ago my IP wound up on UCEPROTECT 
>> level 2. Yes, I know how the UCEPROTECT lists work, but the point is that I 
>> never used to find my IP on those lists, but now it happens every few 
>> months. I have to think something has happened to cause more spammers to use 
>> these providers.
>> 
>> As for incoming Email, I'd like for my own SMTP server to be able to 
>> continue handling it. The reason is that I don't want some other Email 
>> provider's spam blocking software deciding what I get to see. I have some 
>> incoming spam control measures in place for specific Email addresses that 
>> tend to receive a lot of spam, but for me and my family members, everything 
>> gets through. Yes this means we get incoming spam that comes our way, but it 
>> also means we don't have to worry about an important incoming message going 
>> missing because it was sent to the spam folder or silently discarded.
>> 
>> Thanks for any thoughts,
>> 
>> Jayson
>> 
>> On 3/16/2024 5:26 AM, Stephen J. Turnbull wrote:
>>> Jayson Smith writes:
>>> 
>>>   > I'm getting really tired of these unexplained blacklistings. Does
>>>   > anyone know of any reliable outgoing Email service providers?
>>> 
>>> What do you mean by that?  Gmail for example allows you (or did allow
>>> you 18 months ago) to validate an alternate address through the usual
>>> "can you read this mail and send back a cookie" dance, and use those
>>> validated addresses in From.
>>> 
>>> Unfortunately, in my experience at least Gmail won't allow you to use
>>> a non-gmail address in From unless you're using their app or browser
>>> client.  Authenticated SMTP to port 587 doesn't cut it for whatever
>>> reason.  The best I could figure out was sending through eg gmail
>>> using From: m...@gmail.com and setting Reply-To.
>>> 
>>>   > Ideally I want to continue to handle my own incoming Email because
>>>   > I don't want someone else's spam blocking software deciding what
>>>   > Emails I receive.
>>> 
>>> I don't know of freemail who allows that, unfortunately.  The closest
>>> I know of is Google, as above.
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