TROUBLESHOOTING TIPS RE: iCLOUD MAIL SERVER DROPOUT

Question

Here's what I learned throughout this and I will post a discussion in a separate thread for the rest of the folk out there.
MYTHS AND FACTS RE: iCLOUD MAIL SERVER DROPOUT- WHAT I'VE LEARNED
Hopefully this troubleshooting helps everyone that has had or having issues, for now and for the future...
Firstly, the Apple system status is a bit of a myth. Because it is a global community of people using iCloud, it does not always update in real time. The Apple techs check this when there is issues, as do the public, so odds are unless every single person is having issues around the globe, then it won't reflect an issue. http://www.apple.com/au/support/systemstatus/
Apple technicians work in territories. For example, I live in Australia so I had to deal with a tech supervisor who looks after Australasia and who is based in Singapore. They don't get a notification if a group of people in Canada are having problems, even if they are identical to mine, unless as above, the whole world is having issues.
CHECK THESE FORUMS as a first step measure to work out if the problem seems to be just you and your account, or a wider community. Particularly before you make any major change to your email accounts, passwords, computers or phones.
If you get an issue in the next week or so (and keep in mind for the future) Error Message: "MY NAME" returned the error "[AUTHENTICATIONFAILED] Authentication failed." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?" and this happens multiple times when you know the password is correct, then odds are that the server is down and you are best to wait it out. Try checking your mail via iCloud to test. If you can send it through there, odds are that the glitch has nothing to do with your password or issues with your account and rather than make changes, try and wait it out.
If all of your folders in your email disappear, if they are IMAP folders, then log into iCloud mail in your web browser to check that they are still there. It just means that your mail client (Mac Mail, Outlook for Mac etc) can't access the IMAP folders via the server. Don't panic until they are gone from every device you use your email on.
Be wary of deleting ANYTHING from your computer unless you are backing it up first. For example, I had a tech guy on the first day of the server drop out, who gave me the wrong advice of deleting EVERYTHING from my keychain. This resulted in me having massive security issues for web browsers and thus, I couldn't log into my iCloud mail in my browser. Not only did I have to re-install my OS Maverick to fix it (which took 10 hours) but I could have muddled through this mess by continuing to work using web mail.
If everyone seems to be having a mail server problem based on online community discussions, then you are not alone and TELL your Apple tech this. Send copies of the links to the various conversations. Push them (nicely) to investigate internally what is going on and don't let them rely on the System support status. It also helps to put in a report to Apple down the track.
Make sure that you can get a copy of Apple tech guys email address. Thankfully, even though I was on the phone to them for in excess of 7 hours over the past two days, I could update my guy via email and also send him screen shots of things that did or didn't work using my iPhone. We would keep in contact and all I would have to do is send him an email and he would call me back straight away. No holding or dealing with any call centre issues, which is probably the only reason why I didn't lose my cool too much.
If you can get into your iCloud through your web browser, you have the options under the inbox and then the little wheel thing down the bottom (preferences) to put a vacation message, like an out of office. Put that on and explain you are having email issues and give another email address or your contact number. At least the people that you need to contact will know that things could get lost in cyberspace. I wish I had of known this earlier.
You can also forward emails emails to another email address under preferences. Also very handy.
Become friends with your tech guy rather than enemies. If you don't feel like your tech guy knows what he's talking about, politely request to speak to a supervisor. I would be having a nervous breakdown right now (small business owner, lost two days of billable hours so I am financially behind) if I didn't have a good relationship with the guy that has been helping me. We are a good team, with me updating him with the information, via these forums, to find a proper solution to the issue and to rectify the wrong information I was given by the previous Apple tech guy I spoke to.
Ask them to replicate your issue on their side of the fence to troubleshoot. For example, my tech guy Levi replicated my issue with websites by intentially removing the system certificate from his computer and he realised that was what the problem was, and thus he could quickly find out how to fix it.
Back up your stuff regularly. It might be annoying but it is peace of mind if know you are only going to lose a minimum of a week's worth of stuff.
Apple has an engineering team and tech guys raise 'tickets' to them with information on what has happened to their clients. I don't know much about this but I would assume it is having the engineering team investigate to stop this happening in future. They can only work with the feedback they get I suppose. I would also suggest doing the Apple Care survey so they also get feedback. We need to explain to them that we are asking for communication first and foremost - whilst it is inconvenient, if we all knew when and where they would be doing server upgrades (which the rumours indicate that this is what happened) then I don't feel everyone would be so frustrated.
Using your computer is like raising a child - you know when something is not right, even if you are not experienced at it yet. Sure, you may not know the lingo but trust your instincts and tell your tech guy. I have learned more in the past two days about computers and Mac's than ever before and I know when I can confidentially say that strange things were happening to my Mac and where Apple went wrong in guiding me. Don't always take a blanket or easy explanation if you don't think it is right; odds are it will result in making changes to your product that do more harm than good.
Keep a record of notes of how much time you have spent on the issue (including phone calls to Apple), what they have told you to do and at what time, changes to passwords, troubleshooting tips and the contact details (and reference numbers) of who you speak to. I'm not sure if Apple provides compensation for these issues or anything along these lines, but I certainly will be informing them so they can try and better their service to me in the future.
Anyway, I hope that helps everyone a bit - these are just things that I have learned and if anyone else has any tips please feel free to add them.

Answer 1

Tried port 465 but it wouldn't work.
Went to our help desk and here's the reply I got (paraphrased slightly cuz the person at the help desk was trying hard to be helpful and I don't want to get him/her in trouble):
I presented this question to the university team and then waited for a long time to get the following reply:
we do not allow relay from non-university IP addresses.
port 25 for smtp is a standard worldwide.
For the most part, that went right over my head and didn’t answer anything, but I hope it means something to you.
I called him to get more clarification, but all I really got out of it was that, if you don’t use exchange which is secure via port 443, then your other option is to use smtp.  And then he said something about how relay, iron ports, and authenticated accounts work together to make it secure.  I know it makes me sound a lot more inept than I am, but all that made little sense to me.  What I gather, is… that by selecting SSL when configuring your client, it makes it so that your login info and mail content is safe.  Sorry, I can’t provide a more cohesive and comprehensive explanation, but I think the bottom line is that they have combined a non-secure protocol with other stuff to make it secure.
So, I'm hoping that checking SSL and using port 25 somehow solves the problem to the satisfaction of our IT professionals at the University ...
Again, thanks for taking the time to educate the rest of us!