Can I set the "Reply-To" header to fill by default?

A week or so, I discovered that bucket-list travel plans I was making by email for a summer European trip had not been responded to by the London UK travel agency office because I had mistyped the username of the agent, triggering a bounce message from the travel agency’s server.

My junk mail folder for my iCloud mail account has been performing fairly well. No, it doesn’t
catch ALL the spam and silly advertising messages, but it RARELY captures messages I want to receive. On this occasion, however, the bounce message lay unread and undiscovered in my Junk Mail Folder, delaying my booking plans and possibly resulting in some deprecation in my planned travel plans options. Looking back (by putting the sender email address user name, “Mail Delivery System” in Apple mail’s “search” window, I discovered a 3 or 4 other bounce messages had been routed that way for a few different reasons, but only in the last few months. Previously, over many years, bounce messages like this had always landed in my inbox.

I posted a question on a popular Apple user’s listserv (which one doesn’t matter), asking if there was anything I could do to improve the routing of bounce messages. Most of the replies were dismissive, along the lines of “don’t misspell your email addresses,” and even those attempting to be helpful were off base; e.g., route everything that doesn’t target someone in your contacts database to your Junk folder.

Looking through all of mail’s settings, I discovered an option that would direct ANY message with my correct “Reply-To” address filled in during message composition to my inbox, but I’ve not found ANY way to autofill that header field with my email address by default. IS there some way to do that for outgoing iCloud email messages?

My understanding is that when composing email with iOS Mail the Reply-to field is automatically filled with your default email address. While composing you can check this by (confusingly) clicking on the cc:bcc field, This expands the header to show/edit the Reply to field.

BTW - I am also finding that the Spam/Junk function behaves differently after recent iOS updates.

I’m currently using my iPad, but starting to compose a new message and clicking on the cc/bcc field doesn’t bring up the Reply To: field. I’m a bit behind in Software Update (17.3.1), but i doubt that would make a difference here.

This feature doesn’t seem to exist on iOS Mail. I don’t know about Mac Mail (I don’t use it), but this is definitely a feature offered by some mail clients. For instance, on Thunderbird, each account can be configured with its own Reply-To address:

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I’m not 100% sure what you’re asking, but if you’re expecting mail servers to bounce messages to your reply-to address, I’m thinking you’ll be disappointed. A bounce is not a reply and I’m feeling confident that mail servers will respond to the actual sender, not the alternative.

That said, you can set default user headers for your messages, perhaps that’s a method you could use to figure out if a message is one that you sent, now being returned. Let us know what you cook up! See:

My mistake - the From field is displayed. But this is normally also the Reply To field when the recipient views the email headers.

David, thanks for that. I’ve never used Thunderbird, but I’m curious about the “recommended text” that Thunderbird displays for the user; i.e., “Recipients will reply to this OTHER address” (emphasis added).

It took me only three iterations activating the menu command “Message:move to inbox” for messages sent with intentionally misspelled email usernames (before the “@”) to change the behavior, so that similar messages would arrive (unfiltered) in my iCloud inbox… Exploring Mail’s settings, I found the following:

(note activation of "perform custom actions)


Because I had just “trained” mail to filter a few “test” malformed messages from my “Junk Folder” to my inbox, I’m a bit less certain filling the Reply-to field with my own email address would accomplish the same, but I’m uncertain whether the INTENDED recipient’s server could replace what I’d entered in the Reply-to field with directions of its own.

For example, at least some ListServ’s do exactly that. Messages SENT to the listserv are placed by my email client in my “Sent” mail folder, but also posted to the list, and if the member has requested that all messages sent to the list (including his/her own) be sent to all list members, another copy is routed back to the sender’s inbox, but the “Reply-to” field in that copy (handled by the list’s server) arrives back in my inbox with that header filled in with a listserv address chosen by the list-mom.

I apologize if my original post was unclear. My issue was that I sent an important message to an intended recipient who was not in my Contacts or Previous Recipients list. To make matters worse, I misspelled the recipients’s email address, thus almost GUARANTEEING that it would bounce. Up until recently, on the rare occasions that I did this, the bounces would come to my inbox, but on this occasion they didn’t (once I’d misspelled the reciipient’s email address, “kindly” auto-repeated the error, and of course THOSE bounces got filtered to my Junk mailbox as well.

So the issue is NOT whether I really sent a message that ends up as a bounce in my junk mailbox, but how to prevent REAL messages that I sent with malformed addresses from being auto-filtered as bounces into my junk folder, where they don’t belong.

But thanks for your suggestion. I hesitate to try the Terminal command to edit my outgoing headers because it’s current for a macOS version already five generations old

That gray text is just documentation. If you don’t enter anything in the field, it shows that text, but doesn’t use a Reply-To header. If you type something in there, that text will be used for the header.

The text is saying that when recipients reply to a message, the reply will be sent to this address instead of to the address you’re sending the message from. Maybe they could have phrased it better, but it’s hard to describe the concept in one short line.

That’s the way bounce-mail lists often work. Messages come from the original senders, but have a Reply-To header that sends replies to the list.

I also see the technique used for digest-style lists, where the From address may be the list administrator’s address, but the Reply-To header is the lists message-posting address.

If you’re trying to reliably filter by mailing list, unfortunately, different list servers do things differently. You need to look at the full headers to see what the software (probably) intends to use.

I’m not sure this will be helpful in any way, but one of the scummy things that dirtbag spammers (redundant, I know) started doing is sending deliberately malformed messages that would cause a bounce message to be generated that forwarded their spew to their intended victim. That caused a lot of probability-based spam filters to start marking bounce messages as spam. So saying you always want all bounce messages to be treated as legitimate probably isn’t what you want, either.

We’re getting into *Mad Magazine “*Spy vs. Spy” territory here, but maybe it’s relevant. My issue is pretty rare for me, and caused by my own carelessness (misspelling an intended recipient’s username (the part in front of the “at” sign in the email address). Perhaps email system servers have become more suspicious of messages that arrive with usernames not already in their systems and can somehow direct the bounce messages to the originating sender’s Junk box. I’m not certain how those remote servers would cause that to happen, but I get “bounce” messages so rarely that when they come, I want to SEE them in my inbox.

I find that it’s good practice to check my spam mailbox at least every other day. It takes only a minute or two to scan the message subjects, and several times a week, I find a misclassified message. After the scan, I nuke it.

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I have started doing as well!