When email deliverability matters – Gmailify.com

After years of using a free Google Workspace account, and after ups and downs with it, due to Google’s decision to kill it and then keep it alive, I decided to move my emails and other files back to my personal Gmail account.

My main reason for using Google Workspace was the ability to use my domain across Google services, mainly concentrating on the ability to send and receive emails within my domain, but still using the Gmail interface.

After extensive work I had done to move my data from Google Workspace back to my Gmail account, I set up an option for me to receive and send emails within my domain.

I chose Cloudflare Email Routing for that purpose and it mainly worked, for almost three years.

Cloudflare Email Routing is designed to receive emails sent to my address at my domain; however, it’s not truly designed for sending them or replying from the email address at the domain.

I implemented a “sort of” hack to be able to send and reply to emails from a domain in Gmail and it worked quite well, until it didn’t.

Implementing hacks to services that are not designed for such purposes may cause problems. Even if it didn’t for a few months, things on the internet change (evolve) and problems occur.

Firstly, I experienced problems with the receipt of messages.

I quickly noticed that some emails had not been delivered and they had been lost forever. Due to various reasons, I needed to figure out a backup plan to get emails back on track and into my inbox.

To resolve this problem, I implemented Multipath Routing in Cloudflare Email Routing by implementing email workers.

Once Cloudflare failed to deliver emails, for various reasons, to my Gmail address, I forced workers to move them to my backup email in Microsoft services (@outlook.com). From there, using Gmailify (from Google) - a service inside Gmail, I synchronised both mailboxes and all messages started flowing back again.

The number of emails that I lost dropped significantly and the backup measures seem to work nicely.

Shortly after, I noticed other issues when I was sending emails. Some recipients started claiming that they never received emails, and others had been noticing that they had been put into spam folders.

Once this started happening rarely, I didn’t bother too much, until I started getting problems with deliverability to emails operated on Microsoft services.

A lot of companies use Microsoft 365 for Business that operate their emails on their domain. Some government organisations also use their solutions (I am using it at my workplace), and the fact that I was sending them emails with some important documents that they never received (as they landed in spam or were quarantined before even being delivered to the recipient) started causing a lot of problems.

The problem was so significant, that the percentage of emails that I sent and emails that were delivered was sometimes like the flip of a coin. That’s very bad and I decided to make a move.

The cause of the problem was the “hack” that I implemented. I had been sending emails from my domain through “Send mail as” in Gmail, but I am still using Cloudflare infrastructure to receive them.

Even though I had the most crucial email security aspects set on my domain DNS records (SPF, DMARC), I still faced an issue.

After investigation, I found a problem that lay in DKIM signatures.

“DKIM is an authentication method that ensures the message was not modified since it was accepted for delivery, as well as that it was authorised by the owner of the domain. It does so by adding a digital signature to the message for both the metadata (headers) as well as the content. The digital signature is based on public cryptography which works with a pair of keys, public and private. The private key is kept secret by the domain owner or the email service, while the public key is exposed in the DNS publicly as a TXT record. Once the receiving side receives the message, the public DKIM key is looked up and used for verifying the digital signature.”

When I send emails from my domain in Google Workspace, the service digitally signs and matches all records with the Google service I have been using. But that was because Google Workspace was directly set at the DNS levels to use their services, including DKIM.

When I was using Cloudflare Email Routing and ordinary Gmail to send emails, Google services were signing emails with their own DKIM signature that didn’t match whatever I set at the DNS level for the domain. This is because personal Gmail doesn’t allow you to set up a custom domain, and as a result, a signature mismatch occurs.

Despite trying various options to bypass that, the fact remains that if I do not sort the DKIM signature, then most Microsoft services will class my emails as “Unverified” and direct them to the Spam folder, or in the worst case scenario (which has been happening very often recently), with very strict spam rules applied, will quarantine the message on their servers and not deliver it, even to the Spam folder, to the recipient.

This is terrible and has started causing, once again, serious issues not only for me but also for other people that I help to use the same approach to set up their emails on their domain.

All of this leads to the point that I need to stop using this service and explore a better solution.

The solution that I always had in mind was Gmailify.com.

Here, do not confuse Gmailify (the Google solution) with Gmailify.com (a service not from Google). Google offers, inside their Gmail account, a service with the same name that is used for linking Outlook and Yahoo accounts with Gmail.

Before Cloudflare Email Forwarding I had been using Google Domains with their free option called Email Routing. But as it goes with Google, they are killing this service and scrapping it, selling it to the highest bidder.

I tend to always explore free solutions before reaching for paid ones. If the free solution does what is asked, then I generally don’t see the reason for paying anyone else.

The free solution sometimes works to a certain extent, and then you need to make a move and decide what’s important.

I need to rely on my emails. The emails that I send must be delivered to their destination, which is a critical matter to me. There are no compromises here.

With every service, some emails may be misclassified and not delivered as intended, but the ratio shall be as low as possible where the majority shall work (be delivered) as intended, unless you are genuinely sending spam.

With my current solution, this had started to become hit-and-miss and the percentage of emails that I sent that were affected was too high to accept.

Gmailify.com service is not free; however, it costs only $6.99 (£5.60 / 28.00zł) for one year per “main” domain.

Some big players are offering this kind of service with similar price ranges, mostly charging per user and typically per month. This quickly becomes very expensive. Here you pay per domain per year without any further restriction on the number of users etc.

After turning off Cloudflare Email Routing and removing redundant DNS settings (mostly SPF and DMARC) I started setting up my domain.

Spoiler alert: The text below is not a guide through this service or even a tutorial on how to set things up. I will not repeat something that is well documented already.

Gmailify.com is set up in a very nice manner. Everything is described to such a great extent that you can easily go from start to finish in less than 15 minutes, so your ability to receive emails will not be affected for too long.

Even if it is longer, generally, servers, if they struggle to deliver, will try to reattempt after a short period, hence the chance that you will miss anything important is slim.

Setting up is limited to adding relevant DNS settings to our domain. Once that is done, we need to set up our main inbox and connect it with your Gmail account so you can receive emails at your domain (through pop.gmailify.com) but also send emails through it using smtp.gmailify.com. No hack is needed.

Their service provides a temporary mailbox, a middleman, from which the Gmail service is grabbing them. They also provide an outbound server for sending emails and, through that, applying relevant signatures so their emails do not look like spam.

The whole setup process can be started and tested throughout the day without the need to pay for your domain. Throughout that day, you have the option to set things up and then decide. I decided very quickly when I noticed that recipients, who typically have problems receiving my emails, started receiving them without any issues.

The best part is that you only need to pay for the main domain.

I have two domains. I have set up my main one and paid for it. The second I added as an alias domain.

Automatically, my user dariusz in domain wieckiewicz.org will inherit access to the second domain in the same manner.

This solution is not set up to manage domains separately. For example, if you want to have dariusz@domain1.com sent to user1 and dariusz@domain2.com sent to a different user, dariusz@ can only be set to the same user (unless you are applying delegation).

To have the option to set users with the same name independently per domain, you need to pay and set up the domains separately.

I am okay with paying for one and having two. I have set up my friend in a similar manner where the main domain is paid for and all others are just additions.

This makes this kind of service even more value for money.

The service is designed with Gmail in mind and only Gmail. There are some limitations to the service, like the ability to send emails from a domain only through a web interface or the official Gmail app on mobile platforms, or not being able to set an email to send from on devices like photocopiers. You can read about all the limitations in the very detailed documentation.

Apart from just a mailbox, you can also set plenty of aliases and use these aliases across Gmail, to send emails through them. Aliases can be in the main domain or even just in the additional domain. The only aspect to remember is when setting “Send email as” that you set an additional domain using authentication login and password for the main domain.

You can also set up delegations, in such a way that one user has his mailbox, where copies of emails sent to them are delivered to other users. This is a good solution for setting up email for kids, which gives you the ability to see what type of emails are sent to them.

During setup, you may experience some problems from time to time, but even when that happens you can count on support from real humans.

I had one issue during the setup of an additional mailbox, and they helped me very swiftly. Then I experienced some problems with passwords and sending emails from aliases, and they were on the ball with it to help me get this sorted.

Customer support, which is unusual for such an inexpensive service, is hard to find in solutions from big players.

Overall, once the service is set up, you forget that it is there, as you are using it through your Gmail account. Logging on to their service is mostly needed when you add additional aliases or want to track some logs.

What I had been missing on Cloudflare Email Routing is a decent monitoring system of emails sent to the domain and sent from the domain. Of course, there are no sent-from-domain stats, as Cloudflare Email Routing is not designed for that, but for emails received, it is still not the best one, especially when emails are failing to be delivered, and you cannot do anything about it.

There is another aspect that is worth mentioning.

The people behind this service reside in Europe (Switzerland), hence, for data processing and privacy, we may be a little less worried, especially now, when we see how things are evolving (in not a good direction) on the other side of the Atlantic Ocean.

I have only been using their service for a few days. I found some mistakes that I made and was able to quickly resolve them with generous help from real human support. After that, I think it will become a “set and forget” service (of course, don’t forget to pay the year after).