Selfhosting email, and sending email to Microsoft.

About once a year one of my outgoing email servers will magically pop up on Microsofts blacklist of email servers. The exact status in SNDS is “Blocked due to user complaints or other evidence of spamming“, which is a bit ironic since the weekly volume of emails that go to Microsoft controlled domains seldom is higher than 5 and they are all personal emails.
The error message the MTA recieves is “550 5.7.1 Unfortunately, messages from [] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3140). You can also refer your provider to” in case anyone ends up here via google.

I’m not going to bitch and moan or attempt to guess why the server ends up on the list since it isn’t something I can influence
 (just submit a support request and wait), instead I’ll post some tips and pointers to useful tools you should be using:

SPFSender Policy Framework
Specify which IPs are allowed too send mail for your domains, also determine what should happen with mail that is recieved from unauthorized IPs.

DKIMDomainKeys Identified Mail
Outgoing mail servers for a domain can sign the emails and thereby allow recipients to verify that the email really came from a valid mail server and is not from a spoofed sender.

DMARCDomain-based Message Authentication, Reporting & Conformance
DMARC allows you to specify policies for domains or subdomains in regards to “what should happen if an email fails DKIM or SPF” and where/if to send reports for Emails recieved by other mail servers.

SNDSSmart Network Data Service
Allows you to monitor the IPs of your mailservers as viewed by the system.

JMRPJunk Email Reporting Program
Forwards the full message with headers of any email marked as “junk” or “phishing”  by users

MX Toolbox
MXtoolbox is a great website for testing your mail server settings, they also have a free_monitoring service for one IP,  so you can get alerted if your IP shows up on a Blacklist.

Last but not least I use the following small script to monitor the status of my servers according to Microsoft. I call the script via a daily cronjob, and if a server is blacklisted, it sends an alert. Go to Automated Data Access first to generate an API key.

And if all else fails and your IP does end up blacklisted in SNDS, you can go here to submit a ticket to get back off (although I’d suggest checking your mail server logs and the status of the IP on other RBLs first, just to make sure).


Setting up multidomain DKIM with Exim

Update November 2018:

A reader contacted me and pointed out that removing the {} around DKIM_DOMAIN solves the errors in the original example I found and had problems using. I’ve updated the code below (line 8) to reflect those changes in case anyone ends up here via google.

He also shared a nifty way to make selector rollovers easier by adding them to the filename:

And last but not least an elegant way to populate the  DKIM_DOMAIN variable:

Original Posting:

I was recently setting up SPF, DKIM and DMARC for multiple domains and was having trouble getting Exim to sign emails for the different domains. I found an article here explaining the steps. But I kept getting the following error in my exim logs:

failed to expand dkim_private_key: missing or misplaced { or }

The suggested configuration was the following:

I’m not quite sure why, but Exim was having trouble using the macros in the following macros, so I ended up changing it to the following snippet instead. If you don’t use DKIM_FILE you can omit it. Also you might want to set DKIM_STRICT to true if you published a DMARC policy that will reject or quarantine email failing the DKIM tests (unset, or “false” tells Exim to send the message unsigned if it ran into problems signing the email). The default setting for DKIM_CANON is “relaxed“, so it also can be omitted.

Other than that, just make sure the exim process has permissions to access the dkim directory and certificate files and everything should work nicely.

Playing around with Exim, Spamassassin, DKIM and SPF

I was playing around with my mail server today and decided to have a look at DKIM and SPF. Jump to the bottom for some useful links. You will have to be able to change TXT entries for your domain/subdomains to do any of this. Sending a mail to will generate an auto-reply with the result of your mail servers settings. I also noticed that Exim wasn’t listening to the IPv6 interface and promptly fixed that, and have received my first mail via IPv6.

Some spamassassin scores for your local/user settings:

Tools & Information:

Exim walkthrough:
Domain specific settings: