A few months ago I came home on a Friday, just like tonight. Only I was stressed beyond belief at 5:15PM. I had sent three emails, one at 9:00AM PST, the other at 11:12AM PST and the final one at 2:00PM PST. I had found out by calling the people I had emailed that they hadn't received my emails.
My computer is a MacBook Pro 13" Retina. I usually run the latest software, in this case it was 10.10.something. And I was using Apple's Mail app (in applications, go to Mail). My company uses Google Apps for work, which is basically corporate gmail without ads, without any creepy spying, and is ridiculously secure and reliable. I get about one problem with send/receive every 2-3 years, compared to my customers with Office 365 who don't know it, but their email is down about 6X per week (yes, I have access to the logs and can see it).
So when I went into my sent folder on the Mac and saw the three emails stuck there, I was at first shocked. I turned off my WiFi and turned it back on again. Three times. Everyone remember all the WiFi problems with Macs? It didn't do any good. I restarted. Made sure I could load a web page and then tried launching Mail again. No good. The three messages were stuck.
I went into gmail.com and logged in with my TechRoom email address. I checked the sent messages. Nothing. The three messages weren't there. They never made it to the cloud server. They were still on my Mac. Now I was mad. Bruce Banner mad.
The problem is, I know too much. I'm trained on the 7 layers. I know the ports that Google uses. I know the servers that Google resolves to. I know the DNS servers that are reliable. I control my home and office networks with Meraki. Nothing escapes me. There's no reason in the world that I should be having this problem.
I called Google Enterprise support out of pure desperation. Did you know that it's impossible to get someone from Apple on the line on a Friday night at 8:00PM PST, but that Google Enterprise support is 24/7/365 around the world, and you don't need to wait for a representative? I ended up speaking with someone who patiently listened to me explain what I just wrote above. She patiently listened to me whimper and whine about how this can't be happening, with everything configured correctly.
When I was done, she explained to me that, officially, Google has no statement regarding Apple Mail. That said, she explained that the correct settings work sometimes with Apple Mail, and other times they dont.
I explained to her that I was confused, and I asked her to clarify. She said that they have noticed at Google across many other cases that, when using Mail (Apple's application) that sometimes the correct settings work, and other times they don't, and that this is a reproducible issue that they have not been able to resolve.
I was silent. After a moment or two (or longer) she asked if I was still there. I said yes, and that I needed a moment to think about this.
What she had just told me, in the most objective way possible, was that, scientifically speaking, the correct settings for email send and receive worked "sometimes" on Apple applications, and "sometimes" didn't. This was reproducible, meaning you can do this on many other computers and get the same irregular results. Use any other application: Chrome (native gmail), Thunderbird, even Outlook (eww). No problems.
Mail simply doesn't work for Gmail.
I've disregarded the last four updates that applied to my computer that affected Mail. That's because that night I decided no matter how long-standing my habit was with Mail that I was giving it up.
I have since moved to Chrome. I love Chrome. It's vastly superior. I run circles around Mail users- no matter how cool they think their workflows are, I have the power of back-end servers doing extremely powerful things for me. I can use Chrome offline, and I have a preview pane on the right. And I have about 1000 plugins available due to labs that Apple can't even scrape the surface of. I had to move to Chrome for my own sanity that night, and to ensure I could remain productive. I'm going to lose customers if my communication breaks down, and that's what Apple Mail was did. Dead line.
Tonight, six months later, I saw the most recent update that Apple posted that hit my MacBook Pro. I saw three updates, and it made me mad. 1) They still haven't made Mail a decent email program, 2) I own two GoPros, and it upsets me that I can't import from it reliably without a software update and 3) why can't Windows Media files play on a Mac?
Does Apple need some money to buy a few devices to test their software with before they ship it?