I've been in the IT field for quite some time, but I've never really dealt with email systems until now. My customer wants to ensure that all outgoing emails go through their email gateway, which is Barracuda. I thought setting this up would be straightforward—create a send connector to Barracuda. However, I've run into an issue with Exclaimer, which we use to add email signatures. Currently, emails are sent to Exclaimer first, then back to Microsoft 365, and only then they are sent out via M365's servers.
I'm concerned about how to configure it so that all emails go through Exclaimer first and then to Barracuda. I'm worried that if I set it up incorrectly, emails might go directly to Barracuda, which would skip the signature process. Additionally, is there anything I should consider regarding DKIM if I send emails through Barracuda? My understanding is that DKIM is applied once the email gets back from Exclaimer before it goes out, as everything seems to be working fine on the M365 side right now.
I know this might be a basic question, but I just want to ensure I do it correctly since I'm stepping into email operations for the first time.
4 Answers
I have a similar setup using Mimecast and CodeTwo for signatures. They have their own connectors that automatically set up transport rules in M365, so it’s pretty seamless. I haven't worked with Exclaimer directly, but I would assume Barracuda has something similar to make the process easier. If not, their support team can definitely guide you through it.
Also, for DKIM with Barracuda, you typically need to create a TXT record for the DNS settings. Don’t stress too much; just make sure everything’s correctly configured!
You got it right on the routing flow! Just to clarify, when you're updating your DNS to enable Barracuda, that should include sending settings for both email services initially. As you transition, you should be able to have both senders without downtime. Just ensure you keep everything organized and check configurations—you’ve got this!
Setting up Exclaimer and Barracuda works smoothly if you route emails correctly. The usual flow is: Sender > Microsoft 365 > Exclaimer > Microsoft 365 > Barracuda > Recipient. When emails reach Exclaimer, it adds the signature and then sends them back to Microsoft 365. To make sure it doesn't loop, keep Exclaimer's rules at the top in the Exchange Admin Center.
To avoid issues, connect the Barracuda in a specific way by creating a rule that only allows emails from valid senders to be routed to it, preventing Microsoft from processing them too early. You can refer to Exclaimer’s support articles for detailed setup instructions, too!
Absolutely, just chain the connectors in this order: Exchange -> Exclaimer -> Barracuda -> Internet. Regarding DKIM, it’s all good as long as Barracuda doesn’t mess with headers or signatures, which is generally the case. Just remember to adjust the priority settings for connectors in Microsoft 365 properly to avoid any mishaps!
Thanks for that! I'm mainly wondering about how to adjust those priority settings. Is it simply about making sure Exclaimer has a higher priority number than the Barracuda connector? And I assume M365 handles the processing order correctly, right?