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Tag: iCloud email

Why My iCloud Email Stopped Working in Outlook for Mac

When your email program suddenly chokes, it’s probably a good idea to first find out if your email provider has updated any of its policies that require you to take action.

Yes, my iCloud emails abruptly stopped showing up in my Microsoft Outlook for Mac program a few days ago. For the record, it was on June 15. My iMac presented a message warning me that something was very wrong and that it might be my password or user ID. But as far as I knew, nothing had changed.

Boy, was I wrong…

June 15 Can be Hazardous to Your Emails
And if you think you don’t need to worry about this particular tech glitch because you don’t use Outlook for Mac for email, be forewarned that this story affects all of your third-party apps that require a password to get to your iCloud email, calendar and contacts.

I scoured the web for possible solutions.
Hours later, I stumbled across this little detail:
(Thanks to 9to5Mac and Lifewire)

As of June 15, 2017, Apple changed its security policies for non-Apple apps. Now, you need to create app-specific passwords through Apple’s enhanced security protocols of “2-step verification” (older system) or “2-factor verification” (newer system).

What this means is you can’t sign into your non-Apple apps using your iCloud password. You’ve got to create app-specific passwords through Apple.

This is not at all a new process. But if you’ve been avoiding Apple’s verification protocols, now you have no choice but to comply or get kicked out of Apple’s ecosystem.

Give a Dad a Chance!
No doubt, better security bolted onto your iCloud account is wicked important. But it would have been nice to know that this was coming.

But as it turns out, Apple sent an email to me on May 16 explaining the change.
I didn’t see that one apparently…

And then I missed the friendly reminder that went out two days before the deadline.
Mea culpa.

So how hard is it to set it all up?
Not at all.

In fact, it’s easy via the Apple ID page, which houses all of your account details and where you can create these à la carte passwords.

Father’s Day Gift from Apple
Look, I know I wasn’t paying attention. And I was given fair warning… twice.

But Apple… did you have to make the deadline right before Father’s Day?!
I mean… chances are there are other dads out there who ran afoul of this change.
I can’t be the only one.

And wouldn’t it be safe to assume we’ve all got other plans on Father’s Day weekend beyond having to spend time trying to figure out how to get our emails working again?

Choosing a different week would have been better.
(Just a pedestrian point of view from one of your faithful users out there in the trenches)

And to all of you ‘IT Guy’ dads out there who dodged this particular bullet, please hear me: If you don’t have the spare time to make your tech updates in a timely manner and hope to keep the status quo going for as long as possible… you can only wait for so long!

And then it catches up with you.
That’s the reality.
Happy Father’s Day.

Now put away your new tie and get to work.
(And read all of your Apple emails!)

The Secret iPhone Setting to Save Your Emails to iCloud

A proud member of the Silent Generation enjoys a Vietnamese coffee with his baby boomer son.  What controversial topic will the boomer be defending today?  Emails are better than faxes.  (shocking!)

A proud member of the Silent Generation enjoys a Vietnamese coffee with his baby boomer son. What controversial topic will the boomer be defending today? Emails are better than faxes. (shocking!)

My father and I often go out to dinner on Thursday nights.
Usually, he hasn’t even put down the menu when he’s already got some important proclamation to make.
Last week, it had to do with his home tech.

He lowers the daily specials menu insert and out of the blue says to me,
“A fax is much better than email!”

I look at him.

“Come on Dad… really?
Sending an email is so much easier.”

“But a fax gives you a hard copy confirmation,” he replies.
“You have proof it’s been received. An email can get lost.”

“Dad…” I scoff…. “Emails don’t get lost.”

He stares with the assured look of an almost octogenarian.

I try not to roll my eyes as he tries to out-tech-talk me.

But even though my father may not be totally up to speed on current home tech, he does know a thing or two.
(Last week, he’d somehow heard about the latest Apple iWatch rumor before I did.)

Sure, he’s usually biased towards technology from the ‘good old days.’
(He still talks about the wonders of the telegram and the McCormick Reaper.)
And he’s certainly not comfortable with figuring out every tech upgrade that comes along.
But his opinion as a tech consumer is as relevant as anyone’s.

He sometimes quotes me a supposed German saying his father taught him-
Too soon, Old.
Too late, Smart.

And I’m old enough now to begin to recognize how true that is!

Dad Has a Point
Even though my father’s fax machine is wicked old tech, it’s still hanging onto its relevance.
You can’t dispute that gripping a fax report confirmation sheet still gives you a little chill of happiness.
It’s your analog security blanket.

The down side is your successfully sent fax may still never get read.
It may forever be buried in some basket brimming with unread faxes.
But you can remain heartened by the fact it still exists in corporeal form.
That’s got to count for something, right?

But come on Dad!
All of this is so yesterday.
(It’s a dated issue from twenty years ago!)

Email is how the world mostly communicates now, Dad.
Heck, even this is a decade-old conversation.
Maybe we should be talking about how texting is killing email.

Here’s what my father would simply say,
“With a fax, I’ve got my confirmation sheet.
What do you get when you send an email?”

And my dad has a point.

If You Send an Email and Nobody Gets It, Did It Ever Exist?
I recently sent out an email on my iPhone using my iCloud account.

A couple days passed, and I didn’t get a response.

Not that this kind of thing is so rare.
Some people take their time getting back to you.

So I sent a follow up email, also through my iPhone.

No bounce back.
Just nothing…

Then I got paranoid.
Did I dream sending the emails?

I suddenly wanted some proof…

In Search of Proof
So how do you know if any of your emails actually get to where they’re supposed to go?

Well, if you see a copy of your email message in your computer’s email program or your webmail account, you’ve got some evidence.

Of course, there’s any number of dangers confronting your fragile email while on its journey.
(Sometimes you’ll get a bounce back report if your email doesn’t make it. Sometimes not.)

But you really can’t protect your email once its leaves the nest.
All you can do is try to make sure it blasts off successfully.

And much like a fax confirmation page, a saved copy of your email message can offer some comfort.

So I sat down at my iMac to confirm my two emails were also showing up in my email program’s ‘Sent Items’ folder.
(I use Microsoft Outlook for Mac 2011, which I recently upgraded to from Entourage.)

I took a look, and my two emails in question…

But I didn’t panic.
(not yet)

So I did a little research into the email settings on my iPhone.

By Default, Your iPhone Doesn’t Save Your Sent Emails to iCloud
Did you know you’ve actually got to tell your iPhone to save your sent iCloud emails to Apple’s mighty mail server?


Otherwise, your iPhone retains your only copy!
(It’s your iCloud account’s default setting.)

So unless you’ve been inclined to check out every iCloud nuance buried in your iPhone’s settings, there’s likely no secondary evidence your emails have ever made it out of your iPhone.

(The small brown paper bag is behind you. Continue reading after you’ve stopped hyperventilating!)

The Secret Setting to Save Your Emails to iCloud
Okay, here’s the simple fix:
The correct setting is buried seven levels down, deep in the IOS 6 Settings App dungeon.

First, click the Settings icon.
Then begin your multi-level journey down the this rabbit hole by clicking-

  1. Mail, Contacts, Calendars
  2. “Your iCloud email account”
  3. Account (at the top)
  4. Advanced- Mail (at the bottom)
  5. Advanced (at the bottom)
  6. Mailbox Behaviors- Sent Items

You’ve finally arrived at your destination.
You’ll see ‘On the Server’
Here is where you’ll need to check off a specific folder for your email to go in the iCloud mail server.
iPhone email settings

I selected “Sent Items,” which seemed like the obvious choice.

Then, I drafted a test email, and voila!
There it was, also on the mail server.

(I feel so much better.)

Apple makes it so easy to save everything else to iCloud.
Why not your emails?
It probably has to do with Apple’s iCloud storage limits
Remember, every saved email counts against your iCloud storage limit.

Too Many Email Addresses Clog Up Your Brain
You might be wondering how come it took me this long to realize I wasn’t saving my emails to iCloud?
I think it’s partly because I hadn’t thought to track down one of my emails lately.

And what further masked the problem is the complication of my multiple email accounts…

  • I’ve passively collected them over the years:
  • Apple gave me one when I bought my first iMac
  • Then another when I bought my old laptop
  • My Optimum service offered me its own branded email
  • Plus, who doesn’t have an extra Gmail or Yahoo address?
  • And the obligatory address for emails you don’t really want to go to die

At first I thought it was great having several email accounts.
I developed a logic years back on how I would use each account.
(Then I forgot what it was.)

The truth is I don’t send out iCloud emails with my iPhone too often.
So I just hadn’t run into the problem yet.

Read Receipt?
I’m sure someone out there is thinking, “If Barrett is so concerned about his emails, why not send them with the ‘Read Receipt’ setting activated?”

Well, I stopped using that Big Brother functionality in Outlook a long time ago, because I felt it was intrusive.
And both Apple’s Mail and Outlook for Mac don’t support it anyway.

Cancel Fax Vs. Email Smackdown
Dad, I can’t claim my emails are any more bulletproof than your faxes.
But at as long as I strong-arm my iPhone into saving my emails to the mail server, I feel my backup plan equals the value of your fax confirmation page.

Beyond that, there’s no way either technology can guarantee a recipient will receive your important communication, let alone read it.


But my father is never one to let one of our debates end in a draw.
I think I know what he would say…



“Check, please!”

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