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After getting a lot of hilarious submissions, and after carefully narrowing it down to 10 great finalists, today we have a winner.

The winner, as selected by you, the citizens of the internet, is “Delete the CEO.”

You can read through all the finalists below.

For more information on how the Enterprise Mobility Suite can help you manage users, devices, apps, and data check out the EMS homepage.

And, if you’d like to see some of these scenarios dramatized, check out these (funny?) videos about Mobile App Management, Access Management, and Information Protection.

The Best of the Worst Tales from Tech Support Finalists

WINNER. Delete the CEO by Adam S.

As the IT manager I’m the go-to for anything wrong with our CEO.  He is extremely paranoid and most of his requests are asinine.  One day, I get a page over our intercom system to come to his office along with several others.

Someone had spoofed his email address and convinced our accounting department to wire transfer a few thousand dollars to their bank account.
 
This was found out and after many frantic phone calls we found that a notification email had been sent to our CEO stating what was happening prior to the money being transferred.  He protested and said he never received it, didn’t know what they were talking about, and didn’t have this “so-called” email.  He protested to the point of threatening the bank.
 
In his paranoia he deletes all emails then deletes them from deleted items.  I had to recover deleted items on his mailbox to find the bank notification of the wire transfer.  Prior to this day he didn’t know that was possible.
 
We were able to have the funds returned but now he purges the contents of his “recover deleted items” so if it ever happens again there will be no trace….

 

Unplug That! by Andrew Q.

I once visited a customer who was having problems with unexplained outages on their servers every evening. When I arrived I noticed that their entire server room (3 racks) was powered by a series of daisy-chained power strips leading back to a single double socket. It turns out that the cleaners were coming in every evening after the office staff had left, and were unplugging one of these final two power strips in order plug in their vacuum cleaner.
 
I suggested that they may wish to consider locking the server room to prevent the cleaners unplugging things – to say nothing of the security issue! Ideally a power supply with a UPS. The customer came up with a more creative solution…
 
The next time I visited they had remodeled the interior of their office. This included knocking down some walls and building a few new ones. They proudly showed me their solution to the problem. Had they sorted out a decent supply? A UPS? Had they locked the door? Had they simply asked the cleaners to use a different socket? Of course not. They had built another wall right on top of the wall with the double socket, with only the two cables coming through from the other side. They had cemented the plugs from the final power strips inside the wall itself!
 
“Let’s see them try and unplug that!” they proudly declared.
 
“What if you need to change the fuse in one of those plugs?” I asked.
 
“Oh $%&#!!!”

 

High touch user by David L.

So we are in the latter stages of migrating our employees off of an older Exchange 2003 on-prem system to Office365. Pretty much all the early adopters and adept users have had their mailboxes moved without much incident. The high-touch users are up next, and I am working with one of the VP’s. After about 15 minutes of back and forth, verifying the URL to OWA, and that he is typing in his username properly, verifying his account is not locked out, and even opening his mailbox from my OWA, the VP states:

VP: “I would prefer that you talk to my wife, and walk through this with her. She is better at computers than me…”…
 
Me: “OK – does she know your password?”
 
VP: “Yes she does”
 
So, after a similar round of back and forth with the VP’s wife – and getting nowhere – I need to break protocol and I asked –

Me: “Ma’am, I hate to ask, but would you mind telling me what password you are typing in?”
 
Wife: “Sure – it is ‘A B C dash dash 5 6 7′”
 
(mind you, the actual password was a standard used while performing the migration, and is partially changed for this story…). We went back and forth a few more times. No luck. Then… wait… “dash dash”?

Me: “Ma’am, can you try using the “equal sign” in place of the dashes?
 
Wife: “Hey! We’re in! You fixed it!”
 
Yep. I did…. I sure did.

 

Tight Security by John G.

Being in IT, I do routine checks of passwords to make sure they aren’t easily guessable. I also spend a lot of time setting up servers. Security is always a top concern, so we lock them down as best we can.
 
So I go over to one of the departments on campus for a meeting. As I walk out of the meeting, I see a sheet on the wall listing everyone’s passwords. The manager told me it was just in case someone was out of the office, another person could get into their computer for them. Yeah…

 

Password File by Nicholas C.

We had a senior supervisor place everyone’s username and password for all of our systems onto a txt file, and placed it into a share drive in case anyone forgot their password or username.
 
We had a lot of desktop backgrounds changed to kittens, and a lot of frowned-upon downloads registered to random people’s accounts. It was a mess!

 

Dubious back-up by James T.

We went to a client to look at providing steps and costs to move their infrastructure from an ancient local server platform to Azure. We looked around lots of their antiquated hardware and software before I spotted it…… a lone white cable trailing from the back of the server cabinet with the end of the cable tied to the front of the rack with a single cable tie. I see the end of the cable terminates in a female USB type A connection. A quick glance to the right confirms my fears…. a complete tray, full of different color, unlabeled USB thumb drives which they are rotating to store backups.
 
I’ve seen some pathetic implementations in my time, but this has to be one of the best. Mainly because the on-site IT manager was firm in his belief that this was a perfectly acceptable solution.

 

Failing Backups by Jeremy H.

Me: “Tech support, may I help you?”
 
User: “Our backups are failing again; you helped us the last two months.  We really need to get this situation resolved”
 
I remembered the call, and had already shipped them a replacement 5 ¼†drive last month, thinking that was the problem.  Each time the monthly backups are attempted, the previous month’s diskette is corrupt and unusable.  We have had to use a new disk every time.  I have tried shipping a new box of diskettes, and a box from a different lot, trying to figure out the cause.
 
Me: “OK, let’s try a new disk again, that seems to work every time.”  And it did.
 
While the backup is working I start asking further questioning since we had pretty much replaced every part of the backup process.
 
Me: “What do you do with the Diskettes after the backup has completed?”
 
User:  “Put them on the filing cabinet”
 
Me: “Is it a secure location?  Do you think someone is messing with them?”
 
User: “It is fairly secure.  This room remains locked with your system until it is time for the backups.”

Me: “OK, sounds good.  Looks like the backup is finished, let’s go ahead and put the diskette back on the filing cabinet.”
 
User: *THUNK*
 
Me: “What was that?”
 
User: “Oh, just the magnet.”
 
Me: “What MAGNET?”
 
User: “The one we use to hang the diskette on the side of the filing cabinet.”
 
Me: …..

 

The wrong time by Patrick B.

Our network time has always been a few minutes slower than our local cellular service time. Occasionally we have a few users who complain that their computer time is incorrect. While working in the accountant’s office computer one day, I noticed a black smudge on the LCD screen over the computer’s time clock. I tried to wipe it away, but had no luck. When I asked the accountant about it, she said “Oh, I blotted out the clock with a permanent marker so I will not look at it with the wrong time.” Really???? You blotted out the clock on the LCD screen with a permanent marker!?!…. Yes, this actually  happened and I wasn’t sure whether to get mad or laugh it off. So, I just laughed. Happy Monday…

 

Grandma WoW by Chris B.

Working in-store computer support. Cute little older woman around 70ish comes in with giant custom computer. I ask what is wrong.
 
Her: “Computer will not boot up. I need it back by Thursday because my raid needs me.”
 
Me: “Excuse me?”
 
Her: “I am the main healer in my guild and we are doing a raid this Thursday night and I just have to be there. Don’t judge. My granddaughter got me into this. I am retired, my husband has passed away and I live alone. I need to have fun somehow.”
 
Me: *slight chuckle* “Very well, I will see what I can do.”
 
I fix the computer and she comes in to pick it up a day later.
 
Me: “You are all set. Tell your guild you can make the raid.”

Her: “Oh you are wonderful.” *Hands me a tinfoil wrapped plate* “I baked some cookies for you. Thank you so much.”

Had a good day when I fixed a little old grandma’s computer so she could go play WoW.

 

Lockdown Bypass by Ed O.

I worked in a highly secure facility. We had policies in place that would lock a system after a specified amount of inactivity. We had one (probably more) users that didn’t like the policy. This one guy went out and purchased an analog watch with a second hand. He then set the watch on his desk and placed his mouse (with a laser) on top of the watch to prevent the system from locking.

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