Email issues with WordPress on a VPS using WPmailSMTP and MXRoute

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martyyn

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#270223 29-Apr-2020 12:19

I just want to check this solution should work before I start looking further into this.

I'm about to put a WordPress site on a Vultr VPS but the owner, for various reasons, wants to keep their email hosted with FreeParking.

My understanding is I can create a "noreply" email address with MXRoute and use their SMTP server with the WPMailSMTP plugin to send contact form enquiries and everyone is happy.

On testing, I receive the enquiries to both my work GSuite and personal Gmail accounts, but the owner receives nothing on their FreeParking account.

Am I missing something obvious at the higher level or is there a better way to solve this ?

danfaulknor

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Prodigi

#2473280 29-Apr-2020 12:26

FreeParking is possibly dropping the email as spam as it's coming in from a domain they're authoritative for, but not from them. I'm assuming DKIM etc is configured for MXRoute, as that's how most mail sending services verify the domain anyway.

Are you able to use FreeParking's SMTP server instead? That will mean that FreeParking is Ok with the email, and all the email comes from the same place.

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martyyn

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#2473297 29-Apr-2020 12:36

Thanks Dan, I was just coming to the same realisation as I think it through properly.

I've had a similar situation previously where I used a clients SMTP server, but for some reason it kept breaking. I think because they were changing the password and not telling me. In the end I had to take over the management of that as well to stop them from fiddling.

Having a WP site send email without using the owners SMTP details just isn't feesable is it ? Assuming they are not using blah@xtra.co.nz for their business email or without updating the SPF records to allow a new server to send email.

TheoM

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#2473362 29-Apr-2020 14:22

martyyn:

Having a WP site send email without using the owners SMTP details just isn't feesable is it ? Assuming they are not using blah@xtra.co.nz for their business email or without updating the SPF records to allow a new server to send email.

It's entirely possible. MXRoute is a great solution (and it's run by jar over on LET). My (personal) favourite though right now is Postmark. I don't think I've ever had to set up SPF or DKIM. It just works. Bear in mind I'm biased towards Postmark because the ruby integrations are prem. Postmark failing there's always SES, SendGrid, and Mailgun (in no particular order)

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BlakJak

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#2474902 1-May-2020 16:49

martyyn:

Thanks Dan, I was just coming to the same realisation as I think it through properly.

I've had a similar situation previously where I used a clients SMTP server, but for some reason it kept breaking. I think because they were changing the password and not telling me. In the end I had to take over the management of that as well to stop them from fiddling.

Having a WP site send email without using the owners SMTP details just isn't feesable is it ? Assuming they are not using blah@xtra.co.nz for their business email or without updating the SPF records to allow a new server to send email.

Not an expert on any of the webhosting elements of this but I know email and DNS pretty well.

Where you send email from is functionally separate from where the domain is 'authoritively hosted'.

Anything that creates an email has to specify an envelope-sender (the email address used as the sender address during the SMTP transaction) and also a From: header (the email address that appears as the From: in the email itself). Importantly, these can be different.

Regardless of where your DNS service is hosted, you can specify MX records (the place to which email sent 'to' your domain, will be sent). You can also provision TXT records in the DNS that will define the places allowed send email on your behalf (so email 'from' your domain). The TXT records enable systems such as SPF, DKIM and DMARC. The simplest is SPF.

Your website can be hosted wherever you like, regardless of where your DNS, MX records live. But the envelope-sender address and (to a slightly lesser degree, but essentially the same) From: need to be set so that the sending platform (your vultr-hosted machine) are authorised. This usually means using your own email domain or subdomain (something you can set up and declare SPF (etc) records for, where your Vultr IP address are included in that declaration) are authorised, OR, or Vultr machine sends it's outbound email through a managed service of some sort, that is itself authorised (so, a mailing list service like Sendgrid or whatever, OR, an SMTP AUTH service (like talking back to your ISP SMTP Server, and letting them send the email onward)).

Example: You own your own domain but subscribe to Office 365. You need to update your SPF record to enable both your 'own stuff' and 'O365' to send email on your behalf.

Example: You host some services in a public cloud such as (say) Oracle Cloud. You need to update your SPF record to enable both your 'own stuff' and 'Oracle Cloud' to send email on your behalf.

Example: You set up a subdomain just for the purpose. Like 'webservice.domainname.co.nz'. You don't need to update your main corporate records in any way, but you may want to create new records for 'webservice.domainname.co.nz' that declare that your webhosting platform is allowed to send email on behalf.

You can't just slap any-old-email-address into your web application config as the 'from' for emails it needs to send. Further, it can't just be your domain name, as you've discovered.
Finally, simply using no-reply@ doesn't solve everything either, you usually want to be able to see if a bounce occurs, so you can gracefully deal with that (and stop sending emails to invalid addresses, perhaps). So even if you want to send emails to which you'll never see any replies, you probably actually want to have a mechanism to troll the replies and pull out the ones that'll negatively be affecting your reputation, and act on them at least.

No signature to see here, move along...

wpcharged

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#2474917 1-May-2020 17:19

This sounds most likely to be an SPF issue, which is a really common misconfiguration when sending emails from a website.

The easiest option would be to use either the default PHP sender on the Vultr server or hook into a client's account at Freeparking using an SMTP plugin, so the emails can be sent from Freeparking instead.

A quick way to check that the SPF record includes the IP you're sending email from is on MX Toolbox

martyyn

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#2476371 4-May-2020 15:11

Thanks @blakjak and @wpcharged.

Yes, updating the SPF is the answer and that's what I intend to do with FreeParking once I get the login details to take care of it.