Setting a Specific Reply-to/From Address in Apple/iOS Mail

I am looking to change the reply or from address on emails on the Mac and iOS. Not simply selecting a different reply to address from my list of accounts, but to an address that does not have a mailbox on my system. I think Apple prevents this, but hoping maybe someone here has a workaround…

I have a virtual email address at a personal domain (call it preferred@mydomain.com). This address is automatically forwarded to my personal email at Apple (call it personal@icloud.com). There is no mailbox at mydomain.com therefore I cannot set up an account Apple mail.

I really try to have people email me at preffered@mydomain.com, but they always see the personal@icloud.com listed as the reply to and often start emailing me directly at that address. If I ever choose to move away from iCloud for my email I won’t be able to simply change my forwarding…

Any solutions to this?

  1. Set up a Gmail account or use one you already have.

  2. Forward your domain email to this account.

  3. Add a Gmail alias of your own domain email address:
    https://support.google.com/mail/answer/22370?hl=en

  4. Add that gmail account to Apple Mail.

Oh, I was excited about this solution, but… Gmail wants to log into my preferred@mydomain.com account and their isn’t one. I do not have an email on that domain, it simply forwards all mail sent there to my personal.icloud.com account.

Apple’s Mac and iOS apps will allow you to have a from address which is different. The problem is that Apple as well as Google’s SMTP servers will not let the app send the message.

I use FastMail for this purpose. I actually have over 400 email addresses. I can compose and send with any of the addresses. However, all messages go out on FastMail’s SMTP server. All received messages wind up in iCloud, Google and FastMail. Think fault tolerant access to messages. I also maintain the multiple repositories due to differences in their respective search capabilities. Although, the search repository I trust the most is a MailSteward Pro MySQL database on my Mac.

2 Likes

Can you go to your domain provider and read your email from their website? Can you reply directly from their console so that your domain address displays in your sent email?

I have a similar forwarding setup with 1and1 (my domain provider) and it works great on Apple Mail on my Mac and iPhone.

No. I cannot read emails at the my domain.com site. It is an extra charge for me to have mailboxes there. My domain is hosted by GoDaddy and I am using the free email forwarding service they offer with most domains. This service is intended for people that have email accounts elsewhere and don’t want to set another up at GoDaddy.

At 1and1 we get one free email address with the domain and the ability to either reply from the console or to have the email forwarded. We also get an smtp (outgoing mail address) to use with a different email client.

I have been eyeing Fastmail for a while to offload my email to a centralised solution I would control. But I’m wondering about privacy – are they good? Also, are these solutions (routing iCloud and other adresses through them) kind of “hacky” or are they reliable? I wouldn’t want to go through the hassle of moving everything if it’s to break in a year for some reason. Thanks!

I’ve been with FastMail since at least 2003. During that period they have proven to be more reliable than corporate provided Exchange/IMAP servers, iCloud, and Google. However, during that period, I believe relatively early, at least 10 years ago, they did have one serious outage, where they were down for the good part of a day. However, I did not lose any email and after that outage they completely reconfigured their data centre to build in additional redundancy. I haven’t experienced an access issue of any type since then.

My original interest in FastMail was because I was a user of the now long gone Mulberry app which had strict compliance with and robust support of IMAP standards. This included such advanced features as server side scripting with sieve.

FastMail is easy to setup with your own domains. In terms of integrating with other mail, that too is rather straight forward and I have never had an issue. I use them with iCloud, Gmail, and corporate accounts. FastMail tends to be my primary. Although, after the outage back in the day, I reconfigured my mail so that all messages were ultimately routed to both FastMail and Google. Although, I very rarely use Google. I have used it a couple of times for search.

FastMail has a better than average iOS app. Although, I tend to use both the Apple Mail app on iOS and Mac. However, on iOS I sometimes use FastMail’s, primarily for search or some IMAP administrative type things.

In terms of my original post in this thread, FastMail supports the concepts of your having an account, aliases, and personalities. Your account has to be with them but your aliases and personalities can be almost anything you would like and there is no requirement that a domain you are using be hosted with them. Essentially, as long as you can authenticate your account with their SMTP server you can send and receive for any identity you have setup with them. Including aliases or personalities which are setup on the fly.

I believe one area in which some criticised there offering was that after the introduction of the iPhone, FastMail was late in being able to support push. I was able to work around this because I also had an iCloud account. FastMail’s server side scripting allowed me to direct messages for which I wanted notifications. It also allowed me to send SMS messages to my phone if I was in a country where I didn’t have data access.

The one feature that I don’t use is their SPAM filtering. Please note this is not because I have any negative information and experience. I am a happy SPAMSIEVE user and I have never felt the need to move away from them. Also, I have a Mac that is running mail.app 24/7. Spamsieve provides instructions for configuring so that you can control its operation remotely via your iPhone. Spamsieve at least initially was well ahead of iCloud, Google or FastMail. So I used Spamsieve and never felt the need to investigate other alternatives. Also, I could use the same solution on all three platforms rather than three platform specific approaches.

In my history with FastMail they were bought at one point by Opera. It didn’t appear to change their focus. Eventually, the FastMail staff bought the company back from Opera. Both transitions going to Opera and spinning out of Opera were without any drama which was apparent to the users of the service.

I would recommend you check out the experiences of others at emaildiscussions.com. There is a FastMail testimonial thread in the FastMail sub-forum there.

2 Likes

Wow. Thank you VERY much for that detailed feedback and writeup. That seems extremely tempting, and I think I’m gonna give it a try. Saving your post for future reference. Thanks again! :slight_smile:

Do you install the profile provided by fastmail or used an app password, and why?