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Email Forwarding Fail and Return to The Legacy G Suite

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About a year ago Google announced the sunsetting of the Legacy G Suite product that was available free of cost to users who had signed up for it many years ago. The idea was to force the freeloaders to migrate to the paid Google Workspace service.

Many users, myself included, were dismayed with the announcement, but I wasn’t a heavy G Suite user except for one area, email. Using G Suite, I had set up custom email addresses for my own domains including @hashemian.com and then had configured rules in G Suite Gmail to forward those emails to my regular Gmail account, so I wouldn’t need to check multiple inboxes. This arrangement had worked fine for years but with the sunset announcement I needed to find an alternative.

That alternative came in the form of Cloudflare’s Email Routing service that had been announced around the same time. This free service works by receiving emails for custom email addresses with custom domains and forwarding them to the user’s inbox of choice. It doesn’t offer its own inbox services nor any outbound email capability, only receive and forward. So I left G Suite behind and migrated to the Cloudflare’s service, forwarding the emails to my regular Gmail inbox.

A few weeks later Google relented to pressure from the Legacy G Suite users and decided to leave the service alone, but that decision was immaterial to me. Cloudflare Email Routing was working just fine for me, or so I'd thought.

I manage a few web servers that email me daily reports on their health and activities, but one day a few weeks ago I received no such reports. After eliminating potential suspects such as server outages, outgoing mail server issues and false spam tagging by Gmail, I checked the Cloudflare Email Routing logs and saw that Gmail was rejecting all emails forwarded by the service. I sent a few test emails and observed that they were being blocked too. The log messages contained this excerpt from Gmail's servers:

Our system has detected that this message is likely suspicious due to the very low reputation of the sending domain. To best protect our users from spam, the message has been blocked. Please visit Why has Gmail blocked my messages? - Gmail Help for more information. p198-20020a3742cf000000b00716d7d76e6jiw831843qkb.198 – gsmtp

Gmail was now indiscriminately blocking all messages sent to my custom emails that were received and forwarded by Cloudflare’s service. But why was this happening after a year? No one can say for sure but my theory is that as Cloudflare was forwarding all types of emails, including spam and phishing, Gmail’s algorithms started to associate Cloudflare’s servers with spam until a certain threshold was reached at which point Gmail blocked all my emails from Cloudflare’s forwarding servers. In my case I was quickly alerted to this fact because the expected daily reports hadn’t arrived, but this sudden and wholesale blocking could have adverse consequences for some who may be unaware of this issue for weeks and miss out on urgent emails.

At this point staying on Cloudflare Email Routing was no longer an option and since I still had access to my legacy G Suite account, I migrated the process back to G Suite with one additional change. Having experienced the downside of email forwarding, I opted to use Gmail’s POP facility to pull the emails into Gmail instead of forwarding them from G Suite. That option can be configured from Gmail’s Settings page. Yes, G Suite and Gmail are both Google products and may be more forgiving of each other’s platforms, but one can’t be sure how far the family bonds go. Gmail algorithms may be agnostic when it comes to blocking spam and may even block G Suite and I didn’t want to take that chance.

So, whom is to blame here for the Cloudflare Email Routing to Gmail failure? Really, no one. Cloudflare was doing its job and so was Gmail trying to protect its users. I could wish that Cloudflare would provide inboxes for its users but that’s asking a lot from a company that’s not in the email business. To do that right would require a considerable amount of technical and human resources in a field that’s already rife with players. It has been a few weeks since I’ve returned to G Suite and all’s well so far. The one downside to POP is that messages do not arrive in real time. No one seems to know how frequently Gmail checks user specified POP servers and there’s no setting for it but I’ve had some messages take up to an hour to arrive, but at least they arrive.

Here are some lessons learned regarding email forwarding,

  • If possible, use the same server or service along with aliases to receive all emails in one inbox. This avoids forwarding and moving messages around making it less likely to lose messages due to technical issues or algorithmic reasons.
  • Be careful with having messages blindly forwarded to platforms that are not under your control such as Gmail, Yahoo Mail, or Outlook. It’s better if you control the receiving email server, such as Exchange Server or Postfix, or if your email service provider grants you unfettered admin control.
  • When possible, consider using email access protocols such as POP and IMAP to pull in messages to your desired inbox instead of forwarding the emails.
  • Set up an automated job to send periodic messages to forwarded email addresses and regularly check for their arrival. This basic monitoring step can uncover reception or delivery issues early so they can be quickly addressed and resolved.

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