Apple Mail Tips, Tricks, and Advice
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Apple Mail Tips, Tricks, and Advice

Hello, everyone, and welcome to the class.
Today we are talking all about Apple Mail tips, tricks, and advice. This is one of those
classes where you might think it’s really, really simple, but we have a ton of different
things that we’re going to be going over today. We are live right now. We have five
hundred people tuning in from literally all over the globe. For any of you out there who are watching
this class after the fact, if you’d ever like to take one of our live classes, they
are a free public service. You can find out more by going to our website at
One thing you might want to do to help you with the schedule is there’s a newsletter
that we put out once a week. You can sign up for it. It’s right at the top of the
homepage. Well, not the very tippy top, but anyways it’s right there. It takes two seconds
to sign up, and no, we don’t sell your information to anyone. Don’t worry about that. We’re talking about Apple Mail. What I did
is before I started this class, I threw out a few poll questions at our live audience
to gauge their knowledge and figure out what things we might need to spend more time on
than others. First thing I want to do is talk about one of the things that seems to confuse
the most people, which is basically there are two different types of email technology
out there. One of them is referred to as POP. The other is referred to as IMAP. The difference
is IMAP syncs. For those of you out there who have problems
where your emails do not sync, let’s say you have a Mac, an iPhone, and an iPad and
you go through and you delete a hundred messages on your computer. Then you go to your iPad,
and they’re all still there. That is a sign that you are using a POP email account. One of my little pieces of advice that I give
all of my clients who I work with privately is that it’s really ridiculous in 2015 to
be with a POP email service. You really need to be with IMAP, especially those of you who
use email in business. After all, not only can you not see what messages you’ve deleted,
you can’t see what you’ve responded to. If you’re anything like me with my ADD-soaked
brain, I can’t remember. Did I already respond to that person or not? Then I’m sending
five responses. It’s a good idea to consider switching to
an IMAP account. I’ll give you a few examples. is one of them. Gmail is another
very popular one. There are other services out there that used to be POP that now support
IMAP, but I tend to steer some of my clients away from. Basically the two universal ones that I tend
to say work for most people are either or Gmail. The difference, as far as which
one I recommend over the other, is if you already have an Apple ID, it might be easier
to use Gmail, because it can get kind of confusing otherwise. For most people, it’s going to
end up being Gmail, but iCloud is another good alternative. I have just basically a million bullet points
here on my screen. I’m just going to shoot through them and show you all these great
little tips and tricks. Here we go. Now please keep in mind that all the email addresses
you’re about to see are all fake, so don’t bother trying to send an email to any of them. First thing is I want to give you two great
tricks to take the people who have sent you emails and add them into your saved contacts.
That way, you can respond to them, or you can write to them very easily, not just from
your computer, but if you’re using iCloud, which hopefully you are, then you can do it
very quickly from those devices as well. I’m going to use myself here as an example, okay?
This is just a link I had to send to myself for people who wanted to give a contribution
to what we do. If you get an email from someone… Forgive
the fact that it has my middle initial here twice. It might be a little hard for some
of you here live right now to see this, but when you put your cursor over someone’s
email address in the message, there’s this little carrot icon. It’s like a downward
pointing arrow. If you click on that with one click, you can hit… Shoot. I’m already
in it. Let’s do a different one. YouTube. Okay? You can add “Add to Contacts.” Really,
really fast way. It saves it into your computer. If you’re using iCloud, it’s also now
going to be in your phone and your iPad as well. Very, very good trick. Now the other thing you may want to consider
doing – I’m going to have to blur this out, I know, in post-production – you’ve
probably been sending email for a while. I did a poll question earlier, and I think it
was maybe eighty percent of the people who are here have already been using Apple Mail.
You have other people who you’ve corresponded with, who you have not saved. There’s a
very easy way with one click to add them once again into your contacts. See up here at the very top, we have file,
edit, view? I want you to go to window. Here under window, the one, two, three, four, fifth
item down is previous recipients. This is going to get you access to every single person
you have previously corresponded with. Okay? It’s going to bring up this giant list.
Now one thing you need to keep in mind here – again, sorry, it’s going to be blurred
out for those of you who are watching this after the class – is that this is also going
to include if you have misspelled an email address. It doesn’t see the difference between
right and wrong. If you meant to send someone an email that ended with, and you
typed in “gmail,com”, that mistake is going to be there as well. Just be aware of
that. One thing you should know: Whenever you see
these rows right here where it has name, email – sorry, columns – name, email, last used,
what this means is that when you click on these, it’s going to sort it by that method.
There’s also this other one right here next to where it says name. If you click on it,
it’s going to show you people who are already in your contacts and people who are not already
in your contacts. Okay? Of course, now I’ve got the spinning pinwheel
of death. Anyways. Dear Tim Cook… What’s going on? Okay. Let’s go back into that. My point that I wanted to show you there – let’s
go right back to where we were – is that if someone here is not in your contacts, you
can click on their name. With one click of the bottom right, you can hit add to contacts.
Very easy, and that will be saved. The other thing I want to mention here is:
have you ever had this problem where you go to type someone’s email address, and it
brings up the wrong email address? That’s also from this list. Let’s say this person
here, whose info is going to be blurred out in post-production, let’s say this was a
bad email address or maybe an old email address. If you click “remove from list,” that
person’s information will no longer show up. It will not be a suggested contact. Okay?
A little trick to be aware of. Next thing I want to do is show you how to
create a signature. This is really great for business to do this, and by the way, I apologize
in advance. We are going to be spending a lot of time here. We’re going to going into
where it says mail at the top left. Second item down is preferences. We have all these
different buttons here. We’re going to go into signatures, which is the second to the
last one here. I want to show you how to create a new signature.
The easiest way to do it is to hit the little plus symbol down here at the bottom. It’s
going to usually just put in a default email address and name, just whatever you’ve told
it is your name. You can delete this info, and you can put in whatever you want. For
example, I know a lot of people want to put, of course, their phone number. Put 555-555-5555.
Very popular phone number these days. You can put in your website address. If you do
that and the person clicks on it, it will go to the web. It will be an active link. One of the things I want to warn you about,
something that has been popular in the past, some people still like it. Personally, I’m
not a fan. Yes, it is possible to copy and paste graphics into this. The problem is it’s
going to show every single outgoing message as having an attachment. It can be a pain for you. It can also be a
pain for people you’re sending it to, because if they go to sort through your messages and
look for the email that had a legitimate attachment, like a document, it’s going to be very difficult
to find. Every single email that you’ve ever sent them is going to appear as having
an attachment. My advice is to probably stay away from that. If you want to change up the font, what you
can do is highlight this text and secondary click. For those of you with a laptop, you’re
going to click with two fingers present on your track pad, or if you want, you can just
hold the control key on your keyboard and click. You can go in here to font, and you
can have it show the fonts. You can change it to whatever you want. Another little trick
I thought I’d show you there. What that’s going to do… Sorry, let me
follow through on that. What that’s going to do is we’re going to be able to make
this appear at the bottom of every new message. Now to make it do it automatically, there’s
two extra steps that you need to do here. What you’re going to do is you’re going
to need to drag… In this case, mine’s called signature two. I’m going to need
to drag this and drop it into whichever email address I’m using. I’ll use Gmail here as the example. I’m
going to drag it and drop it. See, now it says, “one signature.” There’s still
one more step. Click on where it says, “your account here,” and below it says, “choose
signature.” This is the part that makes it automatic. Click signature number two.
If I close this window out and create a new message, there it is. You just put your message
above that. That’s a little bit about creating a signature. For those of you who have questions
about that, we can come back to that later on. The next thing I want to mention is a great
trick for those of you who are emailed forms and need to add a signature to that form.
What a lot of people will do at this point is print out the email. They’ll sign it.
They’ll scan it back into their computer and then send it. There is a much, much easier
way to do this. I keep forgetting to do this part ahead of time, so give me two seconds
to whip up a document that I can use as an example here. That was from showing how to
dictate. Okay. Let’s just put together a fake informative
letter. I’m going to save this as a PDF. PDF is a very common type of file format.
Basically what a PDF does, it’s basically an image of a document. The point is that
it’s locked, so a lot of times when you’re dealing with a medical form, something like
that, it’s usually going to be a PDF. I have here on my desktop an untitled document,
and I just want you to pretend that this was something that someone emailed to me that
needs my signature. I’m going to double click on it, and it’s going to open in preview.
If you go to do this, and it does not open in preview, you can secondary click. You will
see here, you have open with. That allows you to change what opens it. This is especially
useful for those of you who use Adobe Reader. Adobe Reader takes over. We can switch it
back to preview, which personally I’m a bigger fan of. Pretend this is a medical form, and I need
to sign my signature right here. Here’s what you do. I’m going to actually do it
with you right now. You’re going to take out a blank piece of paper, and you’re going
to sign your name. Very simple, right? I’m going to unlock my webcam for just a moment. Here’s what you’re going to do. See here
at the very top of the document, we have this little toolbox icon? You’re going to click
on that. It gives you this little dropdown. Check this out right here. See this one that
looks a little bit like a signature? That’s exactly what that is. Ignore what’s going
to pop up. Oh, never mind. What you can do here is you can actually sign
your name on your trackpad. I don’t recommend it. Use your camera. Forgive me. I haven’t
shaved this morning. I should have thought of this ahead of time. Hi everyone! All right.
Here we have a piece of paper, signature. You might be able to see. I’m going to trace
it out. There is a thin blue line right here. You want to make sure that when you hold the
piece of paper up to your webcam, you want to make sure it’s right on that line. Here
we go. Let’s try to do it. That’s not my real
signature, by the way. Now this is the tricky part, is being able to do this and also see
the line. I’ll give you a little preview. I don’t know if that did it or not. Sorry.
Very, very hard for me to do this with my angle. There we go. When you’re done, hit done.
Okay. It cut it off there, because I was stretching. What’s it’s going to do at this point
is it saved that signature to your computer, so you no longer have to print out that document.
All you need to do is, when you need a signature, just go to this icon and click on that signature. Check it out. I can resize it by grabbing
any of these corners. I can make it as big or small as I want, and that is legal. That
is a legal signature. At this point, you just save this document and email it back to the
person. There, I just saved you a ton of paper, for those of you who have those kind of things
that you have to do. Okay. Let’s get out of that. Let me open
up my notes here. By the way, the only reason why you saw a bunch of little debris around
my signature is my notes were on the other side and they bled through. Ignore that. Next thing I want to show you how to do is
use rules in Apple Mail. Let’s go in… Sorry. Let’s go back to mail. We’re going
to go back to preferences. Now there’s a whole bunch of different types of rules out
there that people use this for, and I have to be very broad when I’m explaining how
this works. I am going to give you the example that I tend to really think this works actually
very well for, which is Viagra. For those of you who get junk mail, which
is… Hold on, let me tell you that, everyone, this is a great trick to try to filter out
some of that junk mail. I’m going to actually delete it, because I’m going to recreate
it. You go into rules, and you’re going to hit add new rule. You can name it whatever
you want. I’m going to actually call it Viagra. What you’re going to do is say if
an email meets these terms and conditions, this is what happens automatically. A lot
of people out there get these stupid Viagra emails. They’re junk, of course. What you
can do is tell the email program that if it detects the word Viagra in subject, to automatically
move it to the trash. Here’s how you do it. This first column
right here, you’ve all these different types of things that you can set. In this case,
I’m going to say if the subject contains the word Viagra. What you might want to do
is… A lot of these companies now, what they’ll do to get around this is they are purposefully
misspelling the word Viagra. You might want to try a few different versions of this. You
can do as many as you want. I’m going to say, instead of Viagra, what
can I say that I’ll get away with? Vi-ag-ra. [laughs] I don’t know. I’m just coming
up with examples here. You can say automatically move the message, or you can say delete the
message, or you can say move the message to the trash. Okay? Whatever. You can do either.
Saying delete is just fine as well. Okay? Automatically, that is going to take place.
Just boom, it’s going to be gone. Other things that people use this for: I know executives
who get just a ton of different emails. Some of them, what they like to do is, if an email
has an attachment or if it has an image, they’ll put it into a special folder. Something like
that. I’m going to show you in just a second here. Actually, that’s next on my list.
You can really do whatever you want. Okay? It’s a good trick for avoiding some junk
mail. I’ll give you a few other junk tricks in a little bit. Next one that we’re going to talk about
is creating a mailbox and a smart mailbox and what’s the difference between the two.
An example… Let me delete this so I can recreate it. An example of the smart mailbox
that a lot of people like is just show me email that came in today. It’s not moving
messages. It’s just a different way to organize them. It’s a different way to find them. What we’re going to do for this is, if you
look at the bottom left corner of my Mac, there’s this little plus symbol. Okay? This
is a fairly universal symbol in all the Apple applications, whether it’s contacts or calendars.
It’s add. Add a new smart mailbox, in this case. Similar to rules, we’re going to tell
it if it meets this term and condition, it’s going to go into this mailbox. I’m going
to just call it today. I’m going to say if the message was received today, move it
into today. There you go. Okay? The Gmail sign-in block, whatever that may
be. It’s very easy way to do it. What I want to show you is something important you
should be aware of here. See this message from Google? Okay. Watch this. I’m going
to go into my main mailbox here. You can see it’s right here. It’s first. Right? When
I delete it from the smart mailbox, check it out. Okay? Actually, I’m sorry. That’s
one from [inaudible][17:22]. That’s an old one. I had two in a row. Okay? If I go back
here, you’ll notice that’s gone. That’s just an old one. It does in fact delete it. The next thing I want to show you is about
folders. Folders are basically just a place where you can store stuff. A lot of people
will store receipts. I personally store all my travel plans in a folder. There’s a couple
different ways to do it. It’s a manual process. We’re going to go, once again, to the plus
symbol, and we’re going to go to new mailbox. Okay? The first thing it’s going to ask you is
where do you want this folder to be. I strongly advise you not to use this option. Here’s
the reason why. If you choose “on my mac,” and you use other devices like an iPhone and
an iPad, you are not going to have access to those messages. Instead, if you use something
like Gmail, just click on where it says Gmail. It will store it in the server. That way,
it synchronizes across all devices. Let’s just call it travel, just as an example. Hit
okay. If you look here on the left hand side, we
have all these default folders, and it just added travel right here. Now what I can do
is I can go through my inbox, and I can manually drag and drop messages from one into the other.
You can also do this, by the way, from your phone. There’s a little button at the bottom
where it says reply. One of them is move, and you can move it into a mailbox. Just a
really easy trick. One question someone had asked me earlier
was about moving folders, like from one email account to the other. Let me show you this.
See how we have some here that are listed for Comcast and some that are listed for Gmail?
You can actually move these around. You can drag and drop mailboxes from one account into
the other. My advice, though, is to do it slowly, because when you do that, it’s got
to synchronize everything in the background with their server. It takes a long time. If
you’re going to move entire folders, do it very slowly. Next thing I want to show you – let’s
see here – is a few different junk tricks. First one is a really, really easy one. By
federal law, at least here in the US, if you get on a junk mail list, they are required
to give you a one click option to unsubscribe. If you scroll to the very bottom of the email,
many times you’ll see it says right here, please unsubscribe here. Here’s a hyperlink. There’s an exception to the rule with this.
If it’s one of those pornographic or Viagra eblast [phonetic][20:00], a lot of those you
cannot actually unsubscribe from. They don’t play by the rules, and unfortunately there’s
no enforcement out there for this kind of stuff. There’s also some backend tricks that you
can use to get out of junk mail. The only downside to these is that they will only run
really if your computer is on. I wish… Tim Cook, if you’re out there, please build
these features into the iOS devices, because that would be really nice. I don’t want
to have to keep my Mac on in order for these rules to work. If you go here into… Once again, we’re
in system preferences. Okay? We have junk mail. Third item. This is what I typically
recommend to most people. Check where it says enable junk mail filtering, and move it to
the junk mailbox. Okay? That way, it’s still there. You can still… You have time to look
through it and make sure that there’s no legitimate email that may have just been accidentally
marked as junk. I would do that. The other thing you may want to do is go here
under accounts, and for each of your email addresses, you have these three tabs: account
information, mailbox behaviors, and advanced. I would go into mailbox behaviors for each
account. If you look at all of these here, this is usually somewhere around what I tend
to recommend for most people. This one might change to never. By storing this information
on the server, which you’ll see I have checked here for every one of these, if I’m on the
go and I don’t have my laptop and I need to possibly see if an email has accidentally
gone into my junk mail, I want to have the ability to retrieve it. That’s why I personally
do this. Now some people for this one right here choose
to do a month old. I completely understand that. It’s actually really not a bad idea.
What this means is that if a message is marked as junk, if it’s one month old, it’s going
to automatically delete itself out. It’s gone. Right? Another thing also here with
trash. Some people, especially those who are not in business, like the trash to automatically
empty after it’s a month old. First of all, you should know email does not take up a lot
of space, despite what you might think. In fact, your iMessages usually take up significantly
more. Calendar also surprisingly takes up a lot of space. I typically recommend saying
to do never here. I will show you how to manually clear it all out in a moment. Okay? What this is going to do is basically when
you get in a message and it comes in as junk, it’s going to go into a special mailbox
here called junk. Depending on… I won’t be able to totally reenact this for you, but
with a lot of these, when they come in, you’ll see at the very top right it says, “Mail
thinks that this message is junk.” You can either leave it, I believe, or say mark as
not junk. If you say mark as not junk, it’s going to automatically, when that person or
company emails you again, it’s going to go into your legitimate inbox. Okay? If you want to move it, by the way, out of
junk, all you literally have to do is drag it and drop it back into your inbox. Whether
yours says inbox or, in my case, it has multiple accounts, don’t worry. We’ll go over how
to set that up in a moment. This is legit. I’ll just use myself here as an example.
I can drag and drop that back into my email. That way, it stays there. Okay? Let’s see here. Next thing I want to do
is show you how to customize the toolbar. Okay? Right up here, this gray section is
a toolbar. Also when you create a new message, this is a toolbar. These can be customized.
For example, people who like to kill the environment – I mean, print emails – if they really
want it, you can add a print button. Okay? All you have to do is once again secondary
click in this area, and you should see this icon and text, icon only, text only, hide
toolbar. If you ever go into your email and you see this… Frankly, I don’t even know
why this is an option. What’s the point, unless you’re trying to prevent yourself
from sending it? Maybe it’s an angry email to your ex. If you ever see this, all you
have to do to fix it is right click in this space – I’m sorry, secondary click – and
change it back to either any of these top options. We have a send button again. The last option, though, is customize. For
example, if I want to add print feature back to a new message, I can take print right here
and drag it and drop it into this top menu bar wherever I want. It’ll just stick there.
Okay? There’s a few other options here. I tend to think that the way it comes by default
is usually pretty good for most people, but if you need any of those options, just know
that they’re all available to you there. The same thing applies to this toolbar right
here. Okay? You can customize. There’s a few more options here in this case. Okay?
For example, there is a one-click add to contacts. I just tend to find it easier to hit the little
arrow instead, which is what I do. Next feature, can I do a quick survey for
those of you who are here live? Oh my God, we have so many questions coming in. Okay.
Quick survey. How many people here know how to dictate? [pauses] Automatic dictation.
[pauses] I’m not entirely surprised that about a little more than a third maybe, maybe
about forty percent do not. All the more importance to go over it. If
you are running a Mac that is running operating system 10.7 or later. By the way, the way
you find out is Apple icon above this Mac. You can dictate to your computer. You don’t
need Dragon dictation. You don’t need any other pieces of software out there. It comes
built into the Mac. As far as how well it does it, the different
features of it, that depends on which version. This is part of the reason why I tend to people
at this date in time, that it’s a good idea to upgrade to Yosemite. If you go into the
Apple icon top left of your Mac, second item down, system preferences, from here go down
towards the middle, towards the bottom. It has dictation and speech. The way you’re
about to see it is how I tend to recommend it to my clients. If you want dictation turned on, use enhanced
dictation. What this allows you to do is to use it when you’re not connected to the
internet. If you’re running extremely low on space, you may not want to use this option. Shortcut. I’ve always referred to this as
a trigger key. Okay? Just my own little terminology. By default, it’s set to function key. That’s
the little key, for most of you, it’s the bottom left of your keyboard that says FN.
Personally, I like to use command twice. That’s my preference, but you can really do whatever
you want. What this means is that when I double tap
my command key, it’s going to start listening to me, and I can just simply talk. Now it
tends to be for me a little bit slow because I am doing a live class right now, but I want
to show you how it works. Even though I’m showing you this in the context of email,
this applies to the entire computer. You could be in Word, Pages, anything, and this will
work. You can see here my cursor is blinking, which
means if I type, it’s going to appear. Okay? What I’m going to do, is I’m just going
to double tap my command key. At that point – it may be a little difficult for you all
to hear it – it’s going to ding at me. Once it dings, I can start speaking. You can
also speak punctuation. You can say, “next paragraph.” When you’re done, you can
either tap your trigger key again, or there’s a little done button that you can click. Let’s
give it a shot. [pauses] Note the microphone at the bottom right. [pauses] Dear Mark Collier [phonetic][27:54]. Comma.
Next paragraph. It was so great having you visit our office in Provincetown, Massachusetts.
Come back any time. Period. Next paragraph. David Cox. [pauses] Cool, right? Like I said, the delay from what
you just saw is usually not that bad. It’s just because I’m supporting five hundred
people right now. There you go. You can dictate that through Facebook, email, whatever you
want. Really, really cool feature, especially when I’m working with some of my clients
who are a bit older. They tend to really love that feature. It just doesn’t work well
when you have the TV on in the background. Let’s hit not save. Next feature I want
to mention briefly, if you want to explore this, we have a whole class on Evernote. For
those of you who have an email – we’ll just call it an email situation – especially
those of you in business, and need to categorize different things, one thing you might want
to be aware of that Evernote gives you the ability to do is Evernote gives you a unique
email address where you can send or forward messages to, which will be saved into Evernote
automatically. For example, if I get emailed from one of
our members about this really great idea for a class, what I will usually do is I tend
to organize my notes in Evernote. I will forward that email to a special email address that
I have saved for my Evernote account. That way, when I open up Evernote, it loads, and
it’s not taking up space anymore in my email. If you want to check that out, you can see
our whole class on Evernote. I’ll put a link in the description of the video. Let’s see here. I want to show you how to
create a second email address. Okay? You’ll see here that we have two listed. A lot of
you may have one. Believe it or not, I got this question from quite a few people. How
do I add a second email account? You can. Go back to preferences. Mail, preferences.
Look down here at the bottom left. Notice we’re under accounts right now. There’s
a little plus symbol right here. Click that little plus symbol, and at this point if you
have any of these services up here, it just means that it has all the settings preprogrammed.
It also has quite a few others. You’ll have to click “add other email account,” so
there is a chance you may need to enter in email server settings. I just want you to
be aware that if you are using some sort of a service, for example GoDaddy or BlueHost
where they give you multiple options, do you want to use POP settings or IMAP. Please,
for the love of God, do IMAP. It’s so much better. If you’re using an email provider, if you’re
using an internet provider like Comcast, At&t or Verizon, a lot of those settings these
days are all automatic. You don’t actually need to know the server settings to get into
that. Just in case any of you out there are in fact using Comcast, since they are kind
of a comglomerate these days, Comcast recently updated from POP to IMAP. If you notice that
your Comcast emails are not syncing, what you have to do is basically save all those
emails into something like a folder. Then delete your email account and recreate it.
It will recreate with the new IMAP settings. You may want to call a Comcast rep to help
you with that, if you need help. Next thing I want to show you here is – let’s
see – deleting multiple emails at once. Some people know how to do it. Some people
don’t. It’s worth reviewing. What I’m about to show you is just simply how to select
multiple emails or multiple files. This works with everything. If I hold the command key
on my Mac, I’m able to select multiple items at once. I can select this and this and this
and this. Okay? If I hit the delete key right now, all of those are gone. I’m going to
undo that. Actually, I won’t. If you have a list of emails that you need
to delete all at once, so they’re all in a row, you can click on the first item, hold
the shift key, click on the last item, and then hit the delete key. One of you emailed
me earlier asking, “How do I wipe out all of the trash in Gmail?” I’m going to show
you a way to do it. The only little word of warning is if you have tens of thousands of
emails, this can overload the server. Anytime you’re making major changes to email, don’t
quit out of it when you’ve finished. It’s still doing things in the background that
you can’t see. Okay? For example, if I want to go into… Let’s
see. I’m sorry, not there. Let’s go into my… [pauses] Where would I have a lot? Okay.
Okay. Trash. Let’s go there. Pretend there’s a lot of emails here. Obviously there aren’t.
What you can do, one trick you should be aware of, is if you hit command A – A as in apple
– that is the universal command for select all. Every single email here is selected.
If you hit command A and then hit delete, it’s deleting everything. Once again, just
please leave the computer on for a while. Depending on how many emails, it might be
an hour even, just so it can sync those changes with Gmail’s server. If you cut it off,
it’s not going to have time to do it, and you’re going to see them all reappear in
front of you. Okay. Next topic. Migrating email. Ooo, this
is a fun one. Not. Migrating email can definitely be a nightmare to people who don’t know
how to do it, so I’m going to try my best to help you out here. I’m going to use this
as the example: moving from Comcast to Gmail. Obviously we’re dealing with a lot of dummy
messages here. Forgive me. I’m just going to move a bunch around, just so I have some
more to play with. When you want to move from one email service
to the other, here’s how I usually recommend doing it. You want to have both accounts in
Apple mail. This Comcast is going to represent the old. This is the account that’s being
closed down. Gmail represents the new account that’s being created. Okay? What you’re going to do is select all of
your Comcast messages, as soon as they sync in the background. I’ll just use this one
in the meantime. Select all. Again command A, and you can drag them and drop them. There
they come. Those are the ones that I just moved over. Okay? Select all. They’re all
there, and we’re going to drag and drop them into Gmail. Okay? By doing that, if this
old option is POP, you’ve just moved it into an IMAP account, so that it’s now going
to sync automatically. What I would then also recommend that you
do is with pretty much every email service out there… No. Every email service out there.
There’s no pretty much. There is a way to access your email through the web or through
a program like Apple Mail. In the case of Comcast, you would be going to
When you sign in through the web, in settings or account options – they use different
terminology – there is a way to auto-forward your messages. What you would do is tell Comcast,
“Hey, if I get a new email in, I don’t want it going to this email account. I want
to auto-forward to my correct email address. The other option some people will use instead
is while you’re in that same screen you would also see an auto responder. Now people
use auto responders a lot of times when they are on vacation. Trust me, every time I send
out an e-blast [phonetic][35:33], I get a million of them. What you can do is automatically
email people back letting them know you are no longer using that email address and here’s
the new email address. The downside to doing that is if a spammer
gets a message back that you’ve changed your email address, guess what? They now know
about it. You’re going to start to receive spam there. I tend to typically recommend
the forward option instead of autoreply. It’s just safer for your own security, and then
what you can do after a couple of months is delete that old account. Okay. That’s a
little bit about moving email accounts. The other thing I want to mention is for some
of you who are PC users. I get this question all the time, and it is a nightmare to deal
with. I want to give you a really strong recommendation. If you are moving from a Windows PC to a Mac,
especially for those of you who use Outlook, Outlook can be a beast to deal with. Outlook
uses this file format called PST, whereas Apple Mail uses a file format called MBOX.
There are plenty of people, when this video goes to the internet and it’s on YouTube,
there’s going to be plenty of people out there who are going to disagree with me. I
am giving you my advice based on what is easy. Okay? It’s not that it’s free, but it
is easy. If you go into Outlook, it is fairly simple
for most people to export all of their information into a PST file. Basically, that PST file
doesn’t just contain your email. It also contains your contacts and your calendars.
There’s a great, great little app. You have to buy it. It’s not inexpensive, but it’s
worth it. If you put a value on your time, it’s worth it. Go to the Apple menu, app store. The name
of the app, which I believe is twenty-nine dollars, is called PST Converter Pro. Okay.
Here it is right here. It’s very, very simple for the average person, believe it or not,
to do this. It’s going to just automatically move all that stuff from the Windows world
into the Mac word. Very, very simple. Like I said, you can do this manually. it
is a nightmare to do it, so, please save yourself a little bit of headache and a few grey hairs
at the same time. Pulling out a few hairs, I should probably say. I want to go over viewing
and layout options. You may have been noticing that up to this point I have been using the
old way of viewing messages, and some of you I’m sure in the questions – in the chat
rather – have asked, “How did you do that?” There are two different basic ways to view
your email in Apple Mail. The first is this list view, which is considered older, or you
can go to the new view. If you go into preferences, we have viewing right here. Note the very
first item which I have checked is classic layout. If I undo it, we get this. If you
ever run into this problem, by the way, this is a good… I didn’t mean for this to happen,
but this is actually a good thing. Where you can’t see the message, there’s a really
thin bar right here with a little dot right there. You can drag this over. Okay? Now I
have my message here. Just adjust the size of the windows. Okay. You’ve got your preview of your message
here. You’ve got your actual message here. For those of you who are curious, I actually
do prefer this view right here. Some people who are just used to the old way, they like
the old way. If you do want it, once again, mail, preferences, viewing, and check this
top option here. That’ll make it look like the traditional method, which was done away
a couple years ago. Let’s see here. Oh, also I want to mention…
Let’s go back to the old way of viewing this for just a moment. There’s one other
thing I want to show you here. For those of you who do like this view, again, maybe very
difficult for those of you who are live to see this. There is a very thin bar that separates
these two areas. If you click it and drag it, you can choose how much space each side
takes up. A lot of people like to have more viewing room for the actual email and less
for the preview. Okay? Another thing about organization: once again,
see we have from, subject, date received. There are other ways to organize it and you
should know that if you click on these, that is going to change how it is organized. When
I search by subject, the email that has a number in it is going to be first, then followed
by A. Right? If I click it again, it’s reversed, so now
W is at the top and 6 is at the bottom. Same goes for who it’s from. You can organize
it alphabetically. Most people organize it by date, which would make sense. If you click
on it once, it’s going to be the most recent email at the top, older ones at the bottom.
If you click it again, it’ll reverse that order. The other methods that you can organize is
if you secondary click in this thin white area, these are other things that you can
organize. You can say show attachments. When I do that, see this one right here, which
has a little paper clip? That’s really just the graphic right there. That’s where, like
I said, if you have a signature, that’s where I can be a real pain in the butt. It’s
going to show that every email has a signature. Okay. A few other option that you can choose right
here just by secondary clicking. Let’s see… Choosing which email address is used when
you create a new message or reply. By default, when you hit reply, it’s going to reply
from that email address. If you have multiple email accounts here – like I have Gmail
and I have Comcast – when I’m clicked on Comcast, it’s just Comcast email that’s
going to be listed here. When I click on Gmail, it’s just Gmail. When I click on inbox,
it’s the two combined. Okay? When you hit reply, it’s going to reply to whichever
email address it was sent to. However, when you create a new message, you
can tell it to use a default address. To do that, go once again back to preferences. This
time, we’re going to go into composing right here. You’ll see right here, send new messages
from. You can choose which account you use. I’ll just use plays well with sharks. For
those of you who are curious, that’s the dummy email address I created for when I was
on shark tank. Hit new message. Okay? Notice it’s from
that email address. If you want to switch it, you can just simply click here and switch
from one to the other. Next thing I want to do is show you about inserting photos and
how to downsize them. I’m going to create a new email here. I’m going to attach a
few photos. There’s a couple different ways. You can
either hit attach and manually find the photo, or you can use photo browser, which is basically
going to launch the photos app. You can go into iPhoto. I had to do a system restoration
last night, so I’m going to use iPhoto right now just to get access to these. I’m going
to pull in a bunch of photos here, way more than the average person would. I’m going
to drag and drop them in. Pretend you didn’t see that. Okay. See this little red thing here? Message
size, 63.9 megabytes. Yeah. That’s not what we call email friendly. In terms of what most
people consider to be courteous, you usually want to try to keep your email to under five
megabytes. Some people will say up to eight. When you do more than that, especially if
you send a lot of photos to someone, if they’re on cellular data and they go to download those
photos, they just blew through a lot of their data just to get your photos. Instead, what you can do is built right into
Apple Mail. It will automatically resize them for you. See right here it says image size?
Just by going from actual to large, check it out. We just went from a giant, giant amount
down to 4.8 megabytes. That’s giant shrinkage. That’s like jumping into the ocean right
now, folks. Yes. I just did that joke right now. If I go from large to medium, you’ll see
it shrinks it down even further. Typically, I actually keep it at large. Insert obvious
joke here. Okay? That’s usually what I like. Again, if you keep it five to eight megabytes,
that’s pretty good. The only real exception to the rule is if the person’s going to
be printing the photos, in which case it might be a better idea to, let’s say, use dropbox
instead to send a group of photos. If you want to learn about that, we have a
great, great class that pairs well with this class all about that. You know how certain
food items pair well together, like chocolate and wine, meat and wine, everything else and
wine? [laughs] Also everything else and chocolate. Dang it, mail! Come back. Okay. We have some
classes that do that, too. One of them is… I just taught a class. It’s called, I want
to say, All About iCloud and Dropbox, and I’ll put a link once again to that class
in the description of this video, for those of you who care to learn more about that.
Dropbox, definitely one of the most important tools for anyone in business, in my opinion.
Let’s see here. Next one, I want to talk about sending to
a group of people. Okay? Now this is tricky, because we have an international crowd here.
Laws are different around the world. If you are a business, and you are emailing all of
your customers, it is actually illegal to do it through just a traditional email. If
you send it to all of them, even if you cc them, that is technically speaking illegal.
The reason why is, first of all, you’re violating privacy laws, because what’s going
to happen is this. I’ll give you a real story of someone who didn’t know this and
accidentally did it. You all probably know. I live in Provincetown,
Massachusetts, the very tip of Cape Cod. We had a business here that I’m a fan of, and
they did just this. They emailed all of their customers. Okay? The problem is that when
you send it to or you cc, which is carbon copy, they can see each other’s’ emails.
Well, one person on that list was not a fan of them. What happened was this person wrote
a really, really nasty note and hit reply to all. Immediately, this business had to
do some serious damage control, because all of their customers just saw this really, really
nasty, negative review. Frankly, it’s probably some of their best customers, since they were
on their email list. If you’re emailing a small group of people,
like let’s say your friends. Let’s say you even have a hundred friends. Please show
some courtesy and use BCC. Blind carbon copy. When you do this, what you want to do is send
it to you. Send it to your own email address, but you’re going to blind carbon copy everyone
else. It’s considered courtesy. Now if you have a lot more than that, more
than a hundred people that you need to email, you might want to consider a service like
the one that we use. I’m going to make this small request here, and I like to be very
open about this. We have an affiliated account with these folks. There’s this great little
service called Mail Chimp. Mail Chimp is competitor to other services out there, like Constant
Contact. I’m just personally a bigger fan of Mail Chimp. I’ve nothing against Constant
Contact. I’ve just been using them longer, and I find them to be pretty good. If you decide to go with Mail Chimp, there
will be a link in the description of the video. You can sign up with them for free. If you
have under two thousand subscribers, it’s free. More than that, you’ve got to pay
for it. Right now, I have to pay over three hundred dollars a month just to email all
of you. The more people you get, the more that price comes up. Then again, we’re talking
tens of thousands of people for me to email. It ends up being worth it. Mail Chimp is a
great, great little service if you’re a business. I strongly recommend you check it
out. Next thing I want to do is something that
someone actually here had emailed me about and I wanted to include in this class, which
is sending an email to a specific group of people. Let’s just pretend that you have,
let’s say, a dinner group. A bunch of people, you all get together. You have a pot luck
or something like that. You just want to very quickly be able to send it to all of them
without having to type each one of their email addresses one at a time. Right? Here’s how you can do it. Go into the contacts
app. Okay? It’s the one that looks like a little brown book right there. Go into all
contacts. What I’m going to do is this. See up here, it says file? We’re going to
go to file, and the second item down is new group. [clears throat] Excuse me. You can
call your group whatever you want. I’m just going to call it dinner group. Okay? From here, you’re going to have to go back
into all contacts. Obviously these are all fake. What you’re going to do is you’re
going to drag and drop your contacts into that group. Okay? I’ve got a bunch of fake
ones here. Oops. Turn this on there. When I go into dinner group, see how all of these
names are here? Now I want to make sure that all of these… Okay, that one doesn’t have
an email address, someone I didn’t delete. That one doesn’t. There should be three
people in this group when we’re done. Okay? Once that group is in contacts, check this
out. You can close out of contacts. Go into mail. I think it’s… There we go. New message.
Instead of typing out their email addresses one at a time, or even their names, I’m
just going to type in the word dinner. Group auto fills in. When I hit the enter key, voila!
All of their names pop up. That will work if I send it to CC or BCC. Pretty cool, right? Next thing I want to show you is something…
Once again, I left this out of the last class. For those of you who are in similar situation
to what I have to go through, where I’m usually having to send the same response to
a million people, this can be a lifesaver. Okay? I want to show you how to create something
which I refer to as a trigger phrase. I’m sure there’s a real name for it, but that’s
just what I use. That’s what I call it. A trigger phrase means that I can type a couple
of key strokes on my keyboard, and it’s going to automatically write. It could be
a sentence. It could be an entire paragraph or a page of text. For example, I could do
a thing… Let me think. Let’s say I want to have a default thank you message to someone
for making a contribution to PC Classes online, right? I could make it so that I type in just
a couple keystrokes, and it sends a complete message with a little thank you note. Here’s how you do it. You actually do it
through system preferences. What’s really cool is this feature syncs. If you have an
iPhone or an iPad, you can do this on every single device and beyond just mail, too. You
can do it in documents. From here, I know it sounds a little weird, you’re going to
actually go into keyboard. From keyboard, you’re going to go into text. Okay? Watch
this. This might be a little bit tricky, but I’m going to try to explain it slowly. I’m
going to hit that little plus symbol at the bottom left. Okay? Replace is your trigger
phrase, and then with is whatever the full message is. Whoever is live here emailing
me, please stop. What I’m going to do is create a phrase.
Let’s say I want to make it… I’m trying to think. [pauses] I’ll just do TY. Okay?
Something you would probably never, ever do something this simple, because TY… No, let’s
do something better. Let’s do thank you, but it’s all one word. That’s probably
a better example. You want this, by the way – I should mention – you want this to
be something you would not normally type. It might mean initials, or it might mean combining
words together. I’m going to combine that with… If you’ll
give me one moment, I’m going to dictate a quick phrase here, just so you can see how
this works. [pauses] Thank you so much for your contribution to support
We work really hard to do a good job, and this money helps us continue to offer our
free live classes to the public. Thank you for being a part of what we’re trying to
do. Period. Okay? That’s there. Now watch this. I click
out of it. I just click out of where that was, and it’s saved. Now when I go into
email… Let’s do this one right here. Let’s just create a new message. Watch this. I type
the word thankyou, space, and it autofills in. Once again, I can do that from my phone.
I can do that from my iPad. Anywhere. It’s a really, really cool feature, and you can
create as many as you want. I’ve done that for – god – I can’t even tell you how
many I’ve had in the past. Unfortunately, one of the ones I have to do more of than
any is explaining to people that I’m not their private tech support. Trying to find
a way to phrase that in a way that is not insulting is very, very difficult. What I would like to do at this point is:
we have a live audience here. We have a lot… Mark has been receiving a lot of questions
from folks, so what I’m going to do is end the class now and respond to those folks.
I just want to say before we go, if you are watching us on YouTube, one of the even easier
ways that you can show a little bit of love is if you hit that like button. In case you
didn’t know it, when you hit the like button on a video, it’s basically your little way
of tipping off YouTube that the video you just watched contains relevant content. It
helps us. It helps them. It’s like a group hug. Okay? [laughs] Hit that like button, if you haven’t already
done so. Subscribe to our YouTube channel. It’s free, folks! You can sign up for our
newsletter on our website at This is David A. Cox with
Class dismissed!

About Ralph Robinson

Read All Posts By Ralph Robinson

100 thoughts on “Apple Mail Tips, Tricks, and Advice

  1. David, Im a 26 year Mac user…And feel Im proficient in many of its nuances. However, I found this video very INFORMATIVE in a very non-threatening way. THANK YOU

  2. Hi, this is a great video. However, I have been looking for an answer to a question and it will be great if you can help please.
    I am thinking of adding my gmail and outlooks accounts to the ios mail on iphone. I already have many folders in both my gmail and outlook accounts to keep things organised and i dont want them to get distorted or to disappear. My question is :-
    Will my gmail and outlook folders remain intact as is if I add these email accounts to 'mail' app / client on ios ?
    This will be the first time i will try it. Look forward to hearing from you.

  3. Great tips, even though the video is a year old. As a recently converted Mac user I need all the help I can get! Sometimes I just get tired of trying to figure it all out (it isn't always so obvious and user-friendly as it seems). Thanks for putting in the work to make this available to so many people!

  4. Hi. I have an icloud account on my macbook air and the same on the iphone. I can send emails on the macbook air and receive emails but later on the iphone I cant seen them, both are IMAP. Has anybody had this problem?.

  5. The box for the signature won't open. It's grey instead of black. Is there some reason for that? Thanks for the class. Very helpful.

  6. COuld you tell me how to not allow archive to duplicate the messages received in gmail? Also, I created mailboxes under gmail and tried to save info to them and they were all erased. Please help.

  7. Great video, thanks. Do you know how to remove safari mail from opening up every time on start up? I did go to system preferences & it is not on open on login. But, I still get the read only apply mail box. Thanks, Ted.

  8. Thank you very much for the video. I would like to know how to double space what I am writing when sending a email?

  9. I used your information to create stationery in mail. But I did several before I got it down pat. How to I remove the bad stationery when I show the list of stationery.

    I want to thank you for all the things I have learned from you.

  10. Hello David – thank you for another informative video.
    I have a question regarding Junk folder on Mac, if you don't. I have been using Mac mail for a while but a day ago or so, my Mail icon in the dock started showing a number of unread messages. There were no unread messages in my Inbox, while my Junk folder was completely empty. It seems that my Junk mail does not reach the Junk folder. Could you please help? Thank you in advance for your time, Judit.

  11. Great class as always David – thank you so much. Most of these things I already knew, but I was looking for information on how to get contacts you know to stop going into the junk folder. Yes I have added them to my "address book" they still go to my junk folder, and all day I'm moving important emails from junk to inbox.
    I did look how to do this through Apple and got that answer – simply add senders name to contact, and did check my the preferences to make sure that box was checked…
    Any advice – or help??? I LOVE using the Mac Mail feature, but this is the only thing that drives me crazy.

  12. 11:02 I would just use DocuSign. I used it for something important, and it was accepted.
    11:40 You don't look that bad to me.
    13:40 I report spam either to SpamCop or to [email protected] I even made a script for it, so all I have to do is select the spam, hit the script, and I'm done.
    20:36 I have that switched off, but junk mail is still filtered. There's a rule you can use which is supposed to override that, but it does not work.
    40:45 I think you meant "It's gonna show that every e-mail has an *attachment*".
    41:23 I think you meant "It's gonna reply to from whichever…".
    43:35 That went over my head.
    43:43 Not obvious to me.
    53:31 What happened there?

  13. thank you for the detailed video, this is my first Mac and wanted to use email for office use. please do let me know how to remove the duplicate email inbox ?

  14. Excellent illustration. Please let me know how I can enhance my knowledge about the computer. I just want to be able to use computer knowledge to understand and do basic services of the computer. Later I want to be learn computer graphic and animation. Could you help. Please reply.

  15. hi. please i need help after i update to os x El Capitan my hotmail dont want open at all in mac mail what i have to do to let it work? thank you

  16. What if you have never, ever deleted an email and now have tons of them? 😀 Is there a quicker way to delete all of them? Also, is there a setting where we can choose to have them deleted automatically after a certain time? Thank you!

  17. Excellent speaker & presentation to the point. The outline was very helpful to refer back. I would be interested retaining you for a best practices consult.

  18. Good information. I can use a typed signature for my e-mail, but i can't use the camera to take a picture of my actual signature. I don't use a track pad. And I use an Imac 2017. Can you help here. Thanks David.

  19. Liked the video. But still one thing which i felt missing is creating tables in this mail mac app. No options i could find. Can anyone help me.

  20. i have 15 gb of data in mail box,,, i would like to take backup of these mails. but i cannot able to export more than 2 gb .mbox file size, how to export my all 15 gb of data. and what is the maximum file size of apple .mbox file size ??? reply pls

  21. Hi.. Thanks for creating and sharing this video. Can you please confirm on how do I recall a msg which has already been sent out. With MS, its easier and the button is on the Tool bar. Where is this functionality available with the Apple Mailbox.

  22. David– you are brilliant–and also seem like a nice guy. I'm also an Editor. Avid. Or I should say was–surrently unemployed. Thank you so much for your very comprehensive video. There are a lot of "teaching" videos out there but sometimes you have no idea what the hell they're talking about or doing. You are very good. that you–you got a new subscriber!

  23. David, I have to send a daily log from my work to quite a few recipients and have been racking my brains trying to save time typing individual names. This podcast has saved that problem and helped with quite a few other queries I had and some I didn't. This is a great service that you provide, I have been subscribed for years now but still,​ come to you for advice. Keep up the great work.

  24. Can you please let me know how to set reminders in my Mail, eg. if I have to set a reminder for one particular mail to remind me to follow up after 3 days how do I set it?

  25. Thank you very much! I just happened to click on another video regarding Apple Mail, and I started watching your video. Learned a lot of things I previously had had no clue about so I really appreciate your tips and tricks.

  26. how to optimise the mailbox, coz when working for official mail receive lot of mail, & the mail receiving gets slow.. need the guidance to optimise the mail box

  27. Thank you for the class on Apple Mail. My operating system crashed and took my computer to a local shop. They backed my data but didnt save my apple mail folders. The folders where saved in my computer. Got my computer back and unfortunately my mail folders are missing. Is there a way I can get them back? Thank you in advance.

  28. Hi, I am migrating from MacBook pro(mid2012 model) to MacBook air 256 gb and all my mails (about 8 inboxes ) are using above 100gb of space on my mac, is there a way that I can transfer or access all my mail boxes through icloud I have 200gb space there? please need your advice urgently

  29. Kathy Holle
    Your tutorials are extremely helpful! I would really appreciate one more!! Something like Rules of the Road with how Rules really work. For example, do they work top-down from the first rule on the list; are there any ways to write complex ones that are like an 'If, Then Else'. It's so easy to trample on your own Rules if you don't know what you are doing!! Thank you again! One of these days I need to make an appointment with you. How do I do that?

  30. how can I determine if a mail account is "smart"? If not how can it be changed to a smart account so that it will be synchronized with my other devices?

  31. Hi David – quick question..I am lending my MacBook Pro to my business colleague and I would like to know if there is a way I can password protect my mail app in the dock so they can't access it. I use Hider 2 for files but would like to restrict the mail app. Any help would be appreciated. Thanks

  32. Do you realize that about 70% of what you are saying is totally irrelevant to the subject at hand? If you'd prepare your presentation properly instead of just plunging in a subject you feel you master, you could squeeze this to 10 minutes. You waste people's time.

  33. If anyone could help, it would be nice. I have this problem since I bought my Mac a few weeks ago, but I couldn't find the solution. Every time I send an email, it appears twice in my sent emails folder. I'm using an email and solutions on internet don't work. Please help! Thanks!

  34. Hi David, Thanks for sharing this video. I have a MacBook Air and I always receive few mails at Trash Box which are regular / normal email. I move those mails to my INBOX manually. I am asking help for permanent solution.

  35. Thank you for shairing and educating. David :o)  
    Q: How do I have all my email accounts show on my Mail desk top screen? Thank you.

  36. Can someone please show me how to disable/remove this app? (the mac mail app the little stamp with the eagle on it) I hate this app, it is nothing but a massive problem and I want it gone.

  37. THANK YOU SO MUCH!! You fixed my display that I've been bothered with for 7 months! Excellent tutorial and clean clear voice. Thank you again!

  38. Thank you so much for being on youtube David! and putting your knowledge out there for us to learn from.
    Your classes are the best and I can get so much more out of my Apple iMac because if you.
    So a BIG THANK YOU from the UK.

  39. David, Thank you so much for your informative You Tube videos. I cannot tell you how much time I have spent on Apple forums trying to find answers, to no avail. You are the best!

  40. This course was SO helpful! And I have been using a Mac since 2013. Even though I knew most of the things I learned important new stuff. I watched all the ads and made a small PayPal donation on your website in order to support you. Thank you so much! I am going to watch more of your courses. Greetings from Bulgaria!

  41. You have a great class. I didn't see it live but I did like it. I do have a question. When I am sending a email I am getting a copy of that same email sent to me. Why? How can I fix that? Thank you. I did subscribe to you.

  42. Hello i have only 1 question in gmail and outlook we can auto schedule or delay the delivery mail can we do it in apple mail too?

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