Server Greeting Timeout on sent mail - Microsoft Servers

Which setting are we talking about now?

Gmail is both ipv4 and ipv6

My ISP doesn’t provide ipv6

Did you have to change a setting on the MiaB to make it ipv4 only?

@stylnchris I guess I maxed out my replies since I am new so I am replying in this message though it is out of order.
So I should put the IPv6 in both public and private settings here? I do have an IPv6 that is also setup with RDNS. I didn’t have them on setup so those values are blank in my conf.

My sever is a bit unique.

I only pass ipv4 dns because I manually do the entries for external dns.

I also host myself, ISP with static IP on a fiber connection.

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I would recommend having both IPv4 and IPv6, I would be configuring IPv6 if my ISP was able to give me an IPv6 address.

root@mail:~# cat /etc/mailinabox.conf

edit with nano or vi or vim

PUBLIC_IPV6=
PRIVATE_IPV6=

sudo mailinabox should reconfigure miab if you blank your entries.

Again, I dont recommend this but if your testing something ?

Ensure you backup your original file / entries…

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Purge queued mail
postqueue -p

Microsoft is deffering your mail as your IP is not warmed up. Take it easy send gradually.

Yandex accepts both IPV4 and IPV6 if you wish to experiment. Don’t mess with gmail they might block you.

Fill in the Microsoft mitigation form as per the instructions above.

If you wish to have an IPV4 only server edit

Otherwise there is a way to only send IPV 4 but accept IPV6 when possible.
sudo nano /etc/postfix/main.cf
smtp_address_preference = ipv4
#smtp_balance_inet_protocols = yes
smtp_mx_address_limit = 0
inet_protocols = all
Comment out balance+inet+protocols to send to IPV6 capable servers, every other time.
If you do that also insert IPV6 in smtp_address_preference =

Thanks for all the help!

I have discovered the issue and will describe here in case anyone else runs into this issue.

The situation was that I was getting messages from my MiaB server stating that my outgoing messages were delayed due to a timeout on the recipient server greeting. I redacted the real addresses and IPs

<email@address>: conversation with mail.mailserver.net[0.0.0.0] timed
    out while receiving the initial server greeting

I thought this was isolated to MSFT serves as I was only seeing this from their services (365 and Hotmail), but eventually other mailservers were having the same issue and I was getting other delayed emails from my server.

With @stylnchris’s help I was able to dig into my config and realized it might be my IPv6 setup on my box. My settings showed blanks in my /etc/mailinabox.conf for the two IPv6 variables.

A little history on the setup of my box: When i first installed the MiaB I did it on a system that did not have an IPv6 RDNS entry. I later set this up and reran the setup, but it is possible that the MiaB setup do not detect that change.

The resolution:
To fix this issue, I manually added my IPv6 values into the /etc/mailinabox.conf and then ran

sudo mailinabox

and let the configurator do its thing. I noticed that some DNS entries were added and when I checked I now had a lot more AAAA records in my DNS entries for my hosted DNS.

I am not sure if the manual entry made the difference, but it seems that my connections to other mailservers was being affected by the inconsistent IPv6 configuration.

Please note that my system status showed green the whole time so I was not aware of any issues with my box setup from the admin dashboard.

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I guess I have one more series of questions for you now… Contabo, would you recommend them?

Which did you sign up for “Cloud VPS 1” ?

Did you end up prepaying for all 12 months? What location did you end up going with? Assuming your in the USA… United States (West)?

Seems for me United States (West) has best latency, then United States (Central), and then United States (East) which is suprising to me since I’m on the east coast.

I’m considering hosting one of my MiaB servers there which will get me IPv6.

So far it has been great. I did month to month since I wasn’t sure how they would be or if I’d have issues with the setup.

They gave me a clean IP right off the bat and it came with IPv6 right out of the gate. I probably could have saved myself a lot of headache by doing a default setup of MiaB but since this was my first pass I did some things out of order and any issues I encountered were self inflicted.

I am in US East 1 (I didn’t check latency though I am on the west coast) and have had no issues with speed.

I also got object storage for cheap and am syncing my backups to it daily. So far I am spending less that $10 a month on my full setup including backup storage (250gb). Since the object storage is S3 compatible it was easy to setup the sync.

Lastly, the dashboard is dated but usable and informative.

Hope that helps!

Oh, and to add some detail, this was the only server I tried for a MiaB server besides an AWS EC2 that didn’t work out because AWS really doesn’t allow port 25 for anyone.

In the past I also ran a linode server that used port 25 for sending transactional emails without issues, but that was before the sale to Akamai so can’t attest to their quality now.

Long and short of it is that I am getting a lot more memory and CPU with Contabo and have had virtually no issues and have had good interactions with their support the one time I used it.

@stylnchris not sure if you saw the two above responses.