11/26/209:00 am 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. Video Transcript: Hi, this is Gary with MacMost.com. Today let me show you some tips for using Mac Mail. MacMost is brought to you thanks to a great group of more than 800 supporters. Go to MacMost.com/patreon. There you can read more about the Patreon Campaign. Join us and get exclusive content and course discounts. The Mac Mail app has a lot of hidden functionality that not even power users know about. Let's start with the simple one. If you want to create an email message that's primarily an attachment, you want to send a file to somebody, you don't have to start with Mail itself. You can simply drag something, like this image here, into the Dock to the Mail app. What this does is automatically open up a new composition window with that file attached and in the message and you're there ready to type who it's to. Now when you attach an image in a mail message you get to decide whether you send the original image or a more compressed version of it. In a lot of cases a compressed version is just fine. If you look over here you could see Image Size and you can choose from Actual Size, and then Small, Medium, or Large depending upon how big the image is. If it's a small image like this one you're not going to have medium or large options. Pay special attention to this. I often get a lot of screenshots that are automatically set to small and they compress the image so much I can't read anything on it. So make sure you're sending something that's appropriate. If you want somebody to get the full resolution image choose the actual size. Otherwise choose one that works best keeping in mind that they might not have as much bandwidth as you do. Now a lot of us suffer from information overload. You're trying to get your work done and you're constantly getting interrupted with new email messages coming in. Well, you can put a stop to that by going to Mail, Preferences, and then going to General. There you can set Check For New Messages from Automatically to Manually. When you set it to manually you then have to click this button for it to fetch email. So now you can wait until you're ready to deal with email before you see what's new. When you're looking at an email message like this and you want to respond you hit the Respond button and you'll usually find that the message is quoted right there. But you can quote only part of the message by selecting that part and then hitting Reply. Notice only the selected part is part of the response. This is especially useful if somebody sends you a lot of information and you just want to answer one specific question in there. Now you can find settings for this in Preferences under Composing. You've got When Quoting Text in Replies or Forwards include all of the original text or just the selected text, if any. Also in Signatures you can control whether the signature is above or below the quoted text. So notice here it's above. So the quoted text is down below which can make it hard for the person to see what question you're responding to. Instead if you uncheck that and then you respond you can see how it places their quoted text above your signature. Now you can simply click down in here and answer their question and it kind of reads more naturally. Whether you're sending a new email or replying to an existing email you can blind copy somebody on that. So normally if I were to add another address in the To field it would go to both people. The same thing if I use CC here which just makes it clear who this is to and who is just getting a copy of it. But if you want to send a hidden copy so the person it's going to has no idea this is also going to another person you can go to View and then turn on bcc Address Field. Now you can enter another email address here. The person the email is going to has no idea it's sent there. Notice in the left sidebar you'll have things like iCloud or maybe Gmail or Yahoo right here identifying each different account that you've got. If you have multiple accounts from the same service, like say multiple Gmail accounts, it could be hard to figure out which one is which. All you need to do is go to Mail Preferences. Then go to Accounts. For each Account look in Account Information and there's a description field. You can change this to whatever you want. So you can call it something more appropriate and then you could see it would change here to reflect your description. Now while you're here take a look at Mailbox Behaviors. The first item here is Drafts Mailbox. Now a lot of people complain they have a problem where they have a Drafts folder that's filled with semi-completed email messages and then you'll see these on your other devices and things as well. What I find is handy to do is change your Drafts mailbox to On My Mac. So your drafts are saved locally not on the server. Another setting to look at is under viewing there's a checkbox here for Smart Addresses. So notice here the Smart Address is checked. I just see the person's name. If you like that fine. But if you turn that off it will change this behavior if I click away and then click this message again you could see now it shows me their name and their email address. When you go to compose a new message and you start typing you'll see some suggestions. Now some of these you may recognize from your Contacts. Some of those aren't in your Contacts. They are taken from emails you've previously received. If you want to edit that list go to Window and then Previous Recipients and then you see a list here. You can go through it. You can select one, or remove it from the list. You can also select one and add it to your Contacts. Now let's say you get an email to you but it really should be handled by somebody else. You want to forward it to somebody. You can use the Forward button here and now it takes that message, it quotes it, allows you to enter in your own message at the top. If that's what you want fine. But if you want to just send this message exactly as it is to somebody else instead go to Message and then Redirect. This then takes the message as it is here and sends it to whoever you specify. Now let's say you're composing a new message and you've attached an image or a pdf document and you want to point something out in the document. You can annotate it right her by clicking on this button and choosing Markup. This brings up Markup Tools. You could do a variety of things like, for instance, add an arrow. Then when you send this that is what the recipient gets. It doesn't change your original image at all. It only changes the one that's sent. This also works with pdf's. You could choose Markup here and then you could markup the pdf with something. We can QuickLook at this pdf here in the message but your original pdf hasn't changed. Next I want to show you a feature called Smart Mailboxes. You can create one by going to Mailbox and then New Smart Mailbox. Now I think this is a misnamed feature. Instead of Smart Mailbox this should be called Smart Search because the best way to use it is if you're performing a search pretty often. You can make it much simpler. Like for instance here you could see I can name this what I want and I could say Contains any message that's from this particular address. But I could also add other criteria. So, for instance, I could say if it's also from this address. So in other words the messages that come from these two. But there are tons of other criteria that you could use as well to build a very intelligent search and save it as a Smart Mailbox. As a matter of fact you'll get one here by default that just Today and it just shows you all of today's messages. So for instance you could create a Smart Mailbox from all the messages coming from a particular address or a particular domain or maybe containing a particular subject and then instead of having to manually organize those into a special mailbox or to perform a search over and over again every time you want to see those you could just go to your Smart Mailbox. Now the Notifications you get when you get a new email could be customized. You go to Mail Preferences and then to General. You could see new Message notifications and you could change it to Inbox Only or Only When you get new email from VIP's, or somebody in your Contacts or you could even use a Smart Mailbox. So you could setup a Smart Mailbox that is specifically to indicate who you're supposed to get Notifications from when you get a new email. Then just use it here. You don't have to even look at that Smart Mailbox. You're just using it as a Notifications filter. In addition to that you should note that you could go to System Preferences and then to Notifications and then from there you could go to Mail and here's where you setup what notifications look like. You could use Banners that will go away automatically or Alerts that stay there. You could determine whether or not they are in Notification Center or whether they are seen on your Lock screen. Whether there's a badge on the app icon, a number that tells you how many new emails you have. Now if you're ever having trouble with email, if you have a mailbox or an account that just doesn't seem to be updating, the first thing you should do is select that mailbox and then go to Mailbox Rebuild. This will rebuild what you see in your Mail app from the information on the server. Also notice here on the sidebar you have Favorites here at the top. So I have Inbox and Sent. But you could see Inbox and Sent are also here under my account. I can put something else. For instance if I wanted to have Archive in Favorites as well I can move that up there. I can then Hide this because everything I really need is up here. You can Control click on these and remove them from your Favorites as well or just drag them out. Now if an email is really important and you want to save a copy of it somewhere outside of Mail all you need to do is drag and drop. You could just drag and drop this to any Finder window. You can see it creates an EML file. I can even select that and hit the spacebar to look at it in QuickLook. If I double click on it it will open it up in the Mail app in a separate window. Now let's say you send an email to somebody but it bounced because their email address was wrong. You don't have to go and recreate the message from scratch. You can select the message from your Sent Mailbox and then go to Message Send Again. That brings up composition window with the exact message you sent before. Then you could just delete the To address there and type a new one and then send it. So here's one last tip. If you want a different way to view your list of emails rather than this method here which shows you everything about that message in a tiny little block you can instead go to the Column View. Go to View, Use Column Layout. Now Column Layout is different in Big Sur than it was in previous versions. It looks more like normal columns that you would see in other apps. You can click and click again to sort the columns. You could adjust the column widths. You can Control click and select other columns to view as well. You could select it to have the message previewed here on the bottom or you could go to View and Show Side Preview and get the preview here on the right side. Drag that line to change how much space is available for the list versus the preview. So I hope you like this look at some Mac Mail tips. Hopefully you're able to use some of these to increase your productivity.Related Subjects: Mail (83 videos) Related Video Tutorials: No related posts. Comments: 44 Responses to “20 Mac Mail Tips And Tricks” Stan May 3 years 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 Gary Rosenzweig 3 years 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 3 years ago Why can't I copy and paste things into a new message ie To: or Subject Gary Rosenzweig 3 years ago Joe: You should be able to. Eric 3 years 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 3 years 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? Gary Rosenzweig 3 years 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 3 years 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? Gary Rosenzweig 3 years 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 3 years 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. Gary Rosenzweig 3 years 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 3 years ago Why can’t we snooze emails to look at later? Michael Marx 3 years 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? Gary Rosenzweig 3 years 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. Gary Rosenzweig 3 years ago Michael: Drag it to the position you want in the message. nick 3 years ago Gary: are there specific reasons for using RTF vs Plain Text email formats? thx Gary Rosenzweig 3 years 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 3 years 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? Gary Rosenzweig 3 years 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 3 years 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? Gary Rosenzweig 3 years 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 3 years 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 3 years 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. Gary Rosenzweig 3 years 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 3 years 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! Gary Rosenzweig 3 years 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 3 years ago I am dragging it to the Dock icon. Robert 3 years 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. ???? Gary Rosenzweig 3 years 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 3 years ago That’s strange...it seems to work with the mouse but not the trackpad. Gary Rosenzweig 3 years 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 3 years 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. Gary Rosenzweig 3 years 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 3 years 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 3 years 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? Gary Rosenzweig 3 years 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 3 years 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. Gary Rosenzweig 3 years 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 3 years 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 Gary Rosenzweig 3 years 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 3 years 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. :-) Gary Rosenzweig 3 years 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 3 years 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. :-) ) Gary Rosenzweig 3 years ago Susan: None that I can think of. You've got two separate accounts at separate services. Comments Closed.