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: 38 Responses to “20 Mac Mail Tips And Tricks”

    Stan May
    2 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

    2 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
    2 months ago

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

    2 months ago

    Joe: You should be able to.

    Eric
    2 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
    2 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?

    2 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
    2 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?

    2 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
    2 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.

    2 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
    2 months ago

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

    Michael Marx
    2 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?

    2 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.

    2 months ago

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

    nick
    2 months ago

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

    2 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
    2 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?

    2 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
    2 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?

    2 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
    2 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
    2 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.

    2 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
    1 month 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!

    1 month 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
    1 month ago

    I am dragging it to the Dock icon.

    Robert
    1 month 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.
    ????

    1 month 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
    1 month ago

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

    1 month 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
    1 month 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.

    1 month 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
    1 month 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
    1 month 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?

    1 month 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
    1 month 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.

    1 month 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.

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