20 Mac Mail Tips And Tricks

Here are some tips to help you get the most out of the the Mac Mail app. Learn how to customize the sidebar, redirect messages, markup images and PDFs and much more.

Comments: 44 Responses to “20 Mac Mail Tips And Tricks”

    Stan May
    11 months ago

    Thanks Gary these tips are really useful. There is one additional thing I was hoping would be addressed. In Big Sur, I can no longer swipe left to delete nor right to mark unread. Did we just lose this functionality or can we turn it on somehow?

    Thanks…stan

    11 months ago

    Stan: Swiping left and right with two fingers on my Trackpad works in Mail to bring up options like Unread and Delete for me. Maybe check your Trackpad settings?

    Joe Grillo
    11 months ago

    Why can’t I copy and paste things into a new message ie To: or Subject

    11 months ago

    Joe: You should be able to.

    Eric
    11 months ago

    My experience is the same a Stan’s. I wonder if he, too, is using Column View with a side preview? Switching out of column view enables the delete and unread swipe gestures again.

    Karl
    11 months ago

    Gary – Does making a Smart Mailbox folder put new messages in both the All Inboxes and the Smart Mailbox folder, or does it move new messages there?

    11 months ago

    Karl: Nothing is “in” the Smart Mailbox. Think of it as a search that you can repeat without having to type in all of the search criteria. The message is “in” whatever mailbox you have it in (depends on the type of email service you have how that works). A Smart Mailbox just shows you email across your mailboxes according to the search criteria.

    Karl
    11 months ago

    Gary – So is there a way to create a rule that moves or copies all emails from a certain email address into its own folder?

    11 months ago

    Karl: Depends on your email service. You usually can do it, but do it on the server, not in the client. Otherwise, it would only take place reliably if you were only getting email on your Mac, and no other device.

    richard morrill
    11 months ago

    great tips but you failed to mention the biggest problem of all: repeat emails (often daily) from merchants who want you back as a customer. There is no option to “unsubscribe”. This has resulted in such a flood of emails that important emails get lost. I looked for a way to automatically delete emails from certain addresses or key words but I cant find it. PLEASE PLEASE HELP. Richard.

    11 months ago

    Richard: Really depends on the email. Any legitimate retailer should offer an unsubscribe link to obey laws. If you search and really can’t find anything, then contact their support. Or call them out on Twitter.

    Rick Conners
    11 months ago

    Why can’t we snooze emails to look at later?

    Michael Marx
    11 months ago

    When I am composing an email reply and want to add a photo or other attachment, mail puts this at the bottom of the pane instead of where I want to insert it. How can I insert an attachment within a mail message instead of at the end?

    11 months ago

    Rick: How would you like that to work, exactly? Many people use their inbox that way. Or, you can create a “handle later” mailbox and drag the messages there. In the past, I’ve asked Siri to “remind me about this email message at X:00” and then Archived the message. The Reminder then has a link to it.

    11 months ago

    Michael: Drag it to the position you want in the message.

    nick
    11 months ago

    Gary: are there specific reasons for using RTF vs Plain Text email formats? thx

    11 months ago

    nick: Plain text is just text. No formatting or anything. Rich text can use formatting, styles, fonts, images in with the text, etc.

    Justine
    11 months ago

    Hi Gary, thanks for these tips! As always, learned something new. My question is about the virtue of keeping 20,000+ emails in the inbox and using Smart boxes to organize. Back in 2010 I would manually move emails into folders and had quite an elaborate system for organizing. When I got my new laptop and operating system, I was encouraged to forgo my manual moves and to instead use smart boxes… but with so many emails in my inbox I feel less organized and vulnerable. What are your thoughts?

    11 months ago

    Justine: 20,000 emails in your inbox. That hurts my brain just to think about. The inbox is supposed to be new stuff. Why not use “Archive” to move that stuff out of the inbox? Have them all in your Archive, and save your inbox for new messages? You can still use Smart Mailboxes too, just without the seizure-inducing idea of 20,000 messages in your inbox. The way I do it is something comes into my inbox (like the notification about your comment here) and I read it, take an action if required, and archive it. Inbox back to zero. If I need an email in the future, I find a search always turns it up easily enough. Searches = Smart Mailboxes, so that’s fine.

    Norm
    11 months ago

    Thanks for tips, especially the tip on Mail Failures. I have one email address that I send and receive mail from frequently. However, their email keeps going to my junk mail box. I have checked the preference under junk mail to exempt “Sender of message in my Contacts”. The name is in my Contacts. I have moved message from Junk Mail Folder to Inbox. Neither of the thinks works. Any suggestions?

    11 months ago

    Norm: It is probably your email service putting the message in your junk mailbox before it ever gets to your Mac. Are you using ISP email? That’s the worst and there may be nothing you can do about it. But if they have a web-based version of their email service, you can log into that and see if you can exclude that email from junk or maybe add it to some contacts list they have there.

    Jim Terrinoni
    11 months ago

    Great job. Clear and concise. Especially like that you showed where in the dialogue boxes all the selections you were making resided

    Michael Marx
    11 months ago

    “Gary: Drag it to the position you want in the message.”

    This does not work for me. Again, I am composing a reply to a message and want to insert a pdf, png, etc. It puts this at the bottom of the thread rather than at the point where I want it.
    I am unable to drag the item to the place I wish to insert it.

    11 months ago

    Michael: Not sure why that would be the case. Are you perhaps composing a plain text message? Try it with a new message instead of a reply to that particular one.

    Robert
    10 months ago

    Hi Gary!
    When I try to drag n drop a .jpg file to the mail app, a small message appears “no available windows”.
    What’s going on?
    Thanks in advance!

    10 months ago

    Robert: Where are you dragging it, exactly? The Dock? A window in the app? The Application icon in the Finder? Experiment with it. Are you perhaps pressing down on the Trackpad forcefully? That error message is usually associated with force-touch on a trackpad in certain situations.

    Robert
    10 months ago

    I am dragging it to the Dock icon.

    Robert
    10 months ago

    I am an experienced user of the trackpad and I tried not to put any pressure. It keeps happening….I still keep getting that message. I even tried rebooting.
    ????

    10 months ago

    Robert: Perhaps see if it happens with another pointing device to rule that out? Otherwise, it may take a firsthand look by an expert to diagnose and fix it.

    Robert
    10 months ago

    That’s strange…it seems to work with the mouse but not the trackpad.

    10 months ago

    Robert: Perhaps a trackpad issue then? Have you tried going to System Preferences, Trackpad and turning some things off, like “Force Click” or “Tap to Click”?

    Brian
    10 months ago

    Hi, Gary. Ever since the Big Sur update the search function in mail is painfully slow. Like, 30 seconds, to pull up the mail from a particular sender. I’ve rebuilt the mailboxes but that hasn’t helped. Any ideas?

    Bonus question: The number of UNREAD messages is larger than the number of total emails in my “All Inbox”. I’m wondering if that has anything to do with the slow search.

    10 months ago

    Brian: Like most things email, it is often more to do with the server than the client. If you are using Gmail for instance, a search calls out to the server. Same for unread counts, etc. So maybe your connection to the email server is a bit slower at the moment?

    Brian
    10 months ago

    Thanks, Gary. Really appreciate it. In the last few hours the numbers have flipped – more in Inbox than Unread. Thanks for the amazing work you do – and for your kind reply.

    Don Nauer
    10 months ago

    Gary
    Been trying to move the mail display panel from the right side to the bottom. It was there on the bottom before I upgraded a while back to OS Catalina which I still use. How can I get it back to the bottom of columns listing emails?

    10 months ago

    Don: So are you looking for Column View? Not sure in Catalina, but in Big Sur you can go to View, Use Column Layout. Then View Show Side/Bottom Preview switches where the preview is located. Also works in standard view in Big Sur too.

    Darren
    10 months ago

    Gary: like Justine above I would just read new messages and then leave them in my inbox. Are you suggesting I should then move them to the archive folder? Where are the archive emails saved, both on MacOS and iOS? Locally on the device or on the host email’s sever? After all these years I’m still learning email best practices.

    10 months ago

    Darren: I use my inbox like. physical desktop inbox. Those are messages I need to deal with ASAP. I deal with them (read, respond, take an action, delete, make a note, add a calendar event, save a receipt, etc) and then archive them. If I have something in my Inbox, then I have something I need to deal with. When my inbox is empty, then my work is done.
    Think of Archived and Inbox emails as both being in your email account. But the Inbox view shows you those you haven’t dealt with yet, and the Archive view shows you the one you have dealt with. Normally (but depending on your settings) you can view your Inbox and your Archive folders on all of your devices. That’s the default for iCloud, Gmail and other similar services.

    Susan
    8 months ago

    Just found you, Gary, and this and the 10 tips were both super useful — and I’ve used Mail for about 11 years now! I can’t find an answer to my specific question anywhere. Would love to see a little video about sidebar FOLDERS and all the do’s and don’t’s. :-) I have 2 different email accounts for work and I manage a lot of different tasks/issues…so I have tons of folders to keep myself organized. At this point, each email account has the same set of folders because there is a lot of cross-ov

    8 months ago

    Susan: You can use folders (mailboxes) as you like. I don’t bother with any mailboxes at all myself. Everything goes into Archive when I am done with it. That saves a ton of time. If I need an old email, I just search for it.

    Susan E Lockwood
    8 months ago

    Hi Gary. Thanks for the quick response! So, what happens in Gmail proper if (in Mail) I take a message sent to email address A and put it in a folder associated with the email address B? I was worried it would freak out and if Mail ever fell apart and I had to use real Gmail it would be a total mess. :-)

    8 months ago

    Susan: You shouldn’t do that. What you are doing then is copying the entire message to your Mac, then adding it to an account on another service, then it is uploaded to that service. Yes, a total mess.

    Susan E Lockwood
    8 months ago

    So then there really is NOT any good way to consolidate — in an organized fashion — email messages from 2 email addresses? (Just putting everything in one Archive folder and hoping the crappy search function will work is a non-starter for me. :-) )

    8 months ago

    Susan: None that I can think of. You’ve got two separate accounts at separate services.

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