A Mac OS upgrade that went wrong, and how I retrieve my precious photos and sanity

So, when we entered 2023, suddenly, my mail and calendar no longer worked for my work mail as it kept asking for my password. After a clarification call to the IT support, I was informed that my workplace decided that the older operating system (OS) on my iMac was no longer acceptable, and I had to upgrade to OS 11 and higher, i.e Big Sur and up.

I was worried about this, as I have been using the current system for ages, and it has served me well. Furthermore, it might break some of my apps, or worse make the entire interface unfriendly. Now, given that it's a Mac, I thought, well, that should not be the case, so I decided to do some backups, wisely as it turned out, on my Time Machines (TM) first. I'm not the devil may care, throw caution to the wind type, so I did three back ups. I was tempted to cut it short, and just rely on one, but this caution proved to be justified ...

Some background, I use a 2015 Retina 27" iMac, with a hybrid drive that I eventually upgraded to a 256 SSD and a 3 Tb HDD when the initial drives broke down. 

So I used the updater app that Apple provided, and after some time, I was on Big Sur. Then things started to get funny... the finder kept freezing, I discovered a couple of important apps did not work, and Music and Apple TV replaced my single app iTunes. That I was not happy with. 

The good news is that my Office 2016 worked, and most of the other apps were ok. But I couldn't get my mail and calendar to work well, so I decided to use the trusty Time Machine to revert. Somehow it could not and then I had to restart my Mac, and use the recovery mode to try and re-install the OS and then use TM to go back to my old system. 

However after a few failed attempts, I realised that the 256 SSD might not have enough space, as it had apps and other stuff on it. 

I then used another hard disk on a new OS install, Monterrey, and whilst it worked, it was slow (portable 5400 rpm HDD). So at least I knew there was hope. And more importantly, I think my data, including my photos were all intact.

Thankfully I had a 1Tb SSD on hard, and this served as my new start up disc. After installing the older time point from my TM, it booted up ok and I thought ok, I'm back.. then I restarted the Mac and initially I got an error message, that did not want to boot up, and I was worried. 

So I realised that the corrupted install on my 256 Gb SSD was messing things up. So you need to press option upon start up to select the new SSD with the OS. Then it will be ok. 

However when I tried to open Photos app, it said that a newer OS had opened my Photo Library file and now I could not open it in OS 15 or Mojave. This was only the beginning of my troubles..

I thought, ok, no issues, I have backed up a copy on another HDD, but it turned out that it was not the same library and the photos only went back to 2020! Now I was in a panic.

So I began searching for ways to open the new Photos Library file and it ranged from using that slow HDD with the Monterrey on it, to sending my entire photos to the iCloud (costly because there was almost 700 Gb of data). 

I first found that you could right-click and open the Photo Library to extract the contents and to my relief, the photos were all there, in the "Originals" and the "Masters" folder. 

I quickly copied them to another HDD. All the past two years' worth of pictures were that, including my precious baby photos. I don't think I could go home if I lost them..

Finally I searched and found a help article that said I could Restore it from a TM. 

So a pause for a quip... 

The devil and Jesus were in a tussle and the devil went to God to ask Him to give them a challenge to compete...

So God told them to write a really complicated piece of code and see who could finish first. The devil pounced on this and began typing furiously and Jesus also began working. 
Halfway through this, there was a power outage and the computers crashed and had to be restarted. When the computers came back on, the devil saw that he had lost all his work, and began cursing in the most foul fashion possible..

However Jesus continued working calmly, and soon finished his coding.

The devil then demanded to know why Jesus could continue whilst he had lost all his data...

God replied "Jesus saves"

And that is also the moral of my story.. 

Make back ups, then make more back ups and most importantly, test them and check your back ups to make sure they actually work.

So I used TM on my 1 Tb SSD Os, chose the last backup and used the Restore function to restore the Photo library that was last saved using the Os Mojave Photo app. 

With abated breath, I opened it with the app - you will need to press the Option button when clicking on the app, and after a rebuild / repair, I found all my photos!

Now again I have two phones with similar photos, so I took the spare first to try and do the sync with my Mac. 

When I tried to sync, it could not find the photos on my iTunes app. Then I had to google again and I realise you need to designate this new library as the system library, so you enter Preferences on the app, and click that. 

Hurray? No.. the initial sync didn't go well and all the photos on my iphone were gone! It seemed that things had gotten worse! I then restarted iTunes and this time the sync went well. Thank God!

I then tried the phone I normally use daily and did the sync with my hands clasped together.. I was praying and...

Thank God, it went well... phew, I am saved. 

So do make several copies, update them, check them and it is never enough