OS X Mail: Using “Send Again”

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I think one of the most underappreciated features of Apple Mail is the “Send Again” command, which you can access in a few different ways. Get to it from the menus after you’ve clicked on a message…

…by right- or Control-clicking on an email…

…or by using the “Send Again” keyboard shortcut (Shift-Command-D) after selecting your message.

Why is this useful, you may ask? Well, it’s a handy way to pass along an email that you’ve already sent without doing a lot of cleanup. I’m sure you’ve noticed that when you forward a message, it by default puts header information in the body of the email and quotes the original text in a different color. 

When you use “Send Again,” though, it re-creates the message without headers or adding new quote levels. 

So if you’re looking to just use the previous email as a template, you can do so without having to copy and paste or edit out unnecessary elements. Just be sure to change the recipients’ email addresses before you hit Send. Note, too, that this works with any message you’ve got, not just ones you’ve sent, so you could select “Send Again” on someone else’s email if you wanted to. Be sure to use that power for good, my friends.

I like to use this as a way to create and access templates in Apple Mail. Some people use drafts for that purpose, and others enjoy the built-in stationery feature (File> Save as Stationery), but I’ve found both methods to be unreliable and, honestly, kinda clunky. So what I do is write a new message, save it as a draft, and then drag it out of my drafts mailbox into a folder I’ve created just for my templates. When I need to reuse a message, I select it and press Shift-Command-D, and blammo! Piping hot new-messagey goodness. 

I have no idea what that last sentence means, by the way. Sometimes I think higher brain functions are not involved in my writing at all. And no, you guys aren’t allowed to comment and agree with that sentiment, OK?

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This will be unbelievably useful.

Mac Help

Another reason to use ‘Send Again’ is if you are sending a mass mailing to say, 500 people. Most internet service providers will not allow you to send that many emails at one time. You’ll need to break up that 500 person list to five 100 person lists.

Send the first 100. Then select ‘Send Again’. Delete the first 100 names from your list and substitute the second 100 names. Send. Repeat until all 500 emails are sent.

Lee Dronick

As to mass emailings I recommend using a service so that you don’t get tagged. I had to do when I worked for the theatre and we emailed to those on our subscriber list. The service vets your content and the providers had vetted the service so that it wasn’t marked as spam. It is not expensive, this is who we used,


Melissa Holt

Thanks for the comments! You’re welcome, geoduck. grin

And Lee, that’s what I do and recommend for mass emails as well. I use the free version of MailChimp, and I like it a lot!


So there is a problem here

On older Mac operating systems…all of them before Mavericks you could just highlight the email and click sent again or use the keyboard command.
Now the email has to be opened and then you can “Send Again” in any of the ways you recommend.

If you do not agree please leave me a comment or respond as I have tried everything to make it work like it used to (not having to open the email to send again)

Melissa Holt

Hey Jonny!

I’m running Mavericks myself, and this works fine; however, you may run into difficulties if you’re viewing messages by conversation (the toggle for which is at View> Organize by Conversation). In that case, you may have to go in and select the particular message in order for “Send Again” to work properly. Otherwise, though, it seems to be fine under 10.9.

Let me know if that doesn’t seem to be the problem for you!



I send a message so it is in the “Sent folder”

I have to open the email again from the “Send” folder to send it again
Highlighting it in the “Sent” folder does nothing, i have to open it then I can send it again easily

If this is not normal what is wrong…?

Thank you

Melissa Holt

Hey Jonny,

I’m not certain, especially if you don’t have conversation view on. If you’d like, you’re welcome to send me some screenshots, and I’ll see if I can help. My contact form is under my name at the top of the page.



I tried it with both “conversion view on” and off

I tried to email you at the address that came up
and it bounced

Email me webrat AT ultronz COM
I tried the other methods of contacting you also with not response so far

I will send you a Quicktime movie or screen shots

I just went through my Mail Preferences and all looked well

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