DKIM - email passing through multiple services - exchange-server

If an email went from my helpdesk system (which has DKIM) to our exchange server to relay (which has DKIM) to our spam filter (which has DKIM) - will anything break?
Which DKIM record record will be used by the receiving party?

Related

Exchange server filters emails with certain urls in the body of a message and message send fails silently?

I have noticed something very odd about certain emails sent on outlook via an exchange server -- it appears if certain URLs and embedded in the message, message send will fail silently. The message will show up in the "sent items" folder, but it is never actually received by the recipient.
I checked in with GoDaddy who supports my Office365 subscription and they confirmed the behavior (they couldn't send successfully send it either, other me or others in their organization) but had no explanation for the behavior.
I have confirmed that the message sends normally if I use one of my gmail accounts through outlook or or an icloud email account. But my two exchange accounts (on different domains) neither send nor receive any email with this particular embedded url:
(Makes no different if sent in plaintext or not). And other emails, with either no urls or even other urls, send normally. Does Microsoft have a problem with foundation? Or with NFTs or something?
https://foundation.app/#NyanCat/foundation/219
This happens to be the NyanCat NFT that sold for ~$700K a while ago, but no idea what it is about simply the presence of the URL in the body of the message to cause it to fail silently when sent or received on an Exchange server. Not sure if impacts other Exchange servers besides GoDaddy's, but does can anybody explain how this even happening or why?

Email goes to spam folder Gmail and outlook while having 10 in mail-tester

I put a lot of effort in perfectionizing my emails in Magento, in mail-tester i even have a 10. But stil the emails (also when i send a not transactional mail) go to spam in gmail and outlook.
Any idea why?
Email deliverability involves a lot of factors so more information is needed to help you. What are all the services you use to send email out other than Magento? Do you do email marketing? Do you get good engagement with your email marketing (opens. clicks) with low bounces? What's the nature of your business and the content you send in the Magento emails and other emails you send out (e.g., marketing emails) even if through other services?
What precisely is in your Sender Policy Framework Record (SPF) record (please post exactly what's in your SPF record for sending domain)? Do you have DKIM implemented with services that send mail on your behalf? Have you implemented DMARC?
Do you send email from a dedicated or shared IP address(s)? Check hosts and IP address for blacklists at mxtoolbox and check your senderscore at senderscore.org.
Do you know if the problem is limited to Magento or do other emails sent from that domain go to spam as well? You may want to set up a test account or two with gmail and outlook.com as it will be handy to have some email addresses to send to that you've never sent to before for testing purposes.
Note: I tried to post this as a comment but it was too many characters.

Exchange 2013 NDR issue for not existed user in a mailing list

I have an Exchange 2013 server.
Faced with a strange issue of email delivery what I can not solve.
Exchange is rejecting email
if one of the recipients is not exist in a domain
Email will be rejected totally and sender will receive NDR for not existing user.
scenario:
Exchange mailboxes user#domain.com // valid user
user1#domain.com //**user mailbox is not exist**
Sending email from external domain to my exchange server:
TO: user#domain.com,user1#domain.com
Reciving NDR Remote Server returned '550 5.1.1 RESOLVER.ADR.RecipNotFound;
valid user didn't receive email also.
email is rejected
.
I start to google and found that How do I reject incoming email for unknown users in MS Exchange 2013?
exchange has a user validation feature that is enabled by default
I disable it on a console restart transport role.
Set-RecipientFilterConfig -RecipientValidationEnabled $false
run the same scenario again
user#domain.com, user1.domain.com
I receive NDR for not existing user.
but email was delivered to valid user.
Is it a normal behavior for exchange?
What is right by RFC deliver for valid users or reject email?
how it will affect our server hit the public spam list?
Does this not reduce our spam filter resistance?
Please advice.
Thank you.
It's normal for Exchange to send an NDR for non existing users. As you already said, this might also trigger some spam lists because you are sending out mails (NDR) to possible spam honey pots.
A better way to do this would be to have your external MTA (the server which accepts the mail from the internet) check the recipients and refuse to accept mail for non existent email addresses. This way you would never have to send out NDR reports, as the server trying to deliver mail would be informed that it cannot deliver and notifies the sender itself.

After merging a Mandrill account into Mailchimp, how can I accept a verification email if my sending domain is not setup to receive emails?

We've been using Mandrill for years to deploy our app's signup confirmation and password reset emails. This has worked perfectly as we've had SPF and DKIM records added to the DNS configuration according to Mandrill's documentation for verifying sending domains.
However, after merging the Mandrill account with a new Mailchimp account--which is mandated by April 27th--it's requiring me to send a verification email to an address at that domain. The problem is that we don't have a mail server set up to receive emails. The domain is only used to send the "noreply#domain.com" emails.
Any ideas on how I might resolve this? Mailchimp is not giving an option to undo the merge, so effectively I have an app that users are not able to sign up for at the moment, which is problematic to say the least.
You'll want to configure at least one mailbox on that domain somehow to receive mail. That's the only way to confirm ownership of the domain.

Setting my own DKIM in Mailchimp

What do i need to send my emails with DKIM , but with my own DKIM signature and no via the 'authenticate this campaign' checkbox.
Mandrill offers a DKIM & SPF steps for setting but Mailchimp doesn't.
Any suggestions?
When you select Mailchimp's checkbox option to authenticate campaign, Mailchimp is able to automatically attach authentication to your email campaigns without you setting up explicit approval on your server because if you look at the headers of the email when you send it, they are never really affiliating with your server. It will appear as though your campaign was sent from:
you#yoursite.com
But if you look closely at the headers of the email you will find something similar to FROM:
From: =?utf-8?Q?you?=you#yoursite.com
And the sender will say something like:
you=yoursite.com#mail94.us2.mcsv.net
So all of the authentication is set up by Mailchimp on Mailchimp's own outbound SMTP servers, there is never really any interaction with your server.. yoursite.com.
Thus, to answer your question, it's impossible to use your own DKIM signature and send your emails via Mailchimp because the emails would have be getting sent from your domain.. but they're not.. they're being sent from any number of hundreds of servers that Mailchimp owns.
For DKIM, as David noted, you just need to enable their checkbox. If you want to use your own domain, and not showing on behalf of, then just update the SPF record that you have and their servers as allowed.
This will allow you to enable DMARC too.

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