Joys and Woes of #Windows-to-#Mac-to-Windows.


Advice here, including some warnings, on changing operating systems from Windows to Apple, or vice-versa. The following post is based on personal experience and I put it out here to help others make a better-informed decision on whether they want iMac or Windows on their desks.

I’ve used both systems. Each has its deficiencies and advantages. After long exposure to Windows, both at home and in the various workplaces I was employed in, I chose a Mac simply because it’s considered the ‘industry’ standard for both writers and photographers, and I indulge in both crafts. When I retired from employment, I used part of my ‘lump sum’ pension to purchase an iMac, the desktop version.

It was a dream fulfilled. It took a while to get used to the so-called intuitive method of working and I was forced to ask, ‘Intuitive for whom?’ as I struggled with several software differences. Eventually, I understood the way the whole thing worked and settled down to produce some work.

All went well for around four and half years. (At this point, I should warn regulars that you might have read the story in the various posts I’ve placed here on my website. You may wish to skip down to the final paragraphs, following the # marker inserted for your convenience)

Last October, the machine began to play up. Eventually, after I’d tried everything I could, using online help and advice, the machine simply stopped working. I took it to a local certified engineer (local being a round trip of 55 miles, at least an hour each way due to road works in the small town that was my destination) for repair.

The machine was away for a few days and the ‘repair’ cost me £90.00. The machine worked well for a few months, though I’d lost some data which was not able to be retrieved.

Then, around the beginning of February, I came to my study to discover the notification that an update had been installed and a restart was needed. As usual, I closed working programs and selected the restart option. What happened next was something of a surprise. The machine went into a wonderful loop, where it made it halfway through the installation and then flicked up a small window with the message that the process could not be completed for unknown reasons. A small green button at the foot of the window suggested I try another restart. Eight attempts later, I realised I was getting nowhere, other than going in circles.

On to my wife’s Windows laptop with an enquiry. The only solution turned out to be one where the OS had to be deleted in ‘safe mode’ and then re-installed. I did this and, for a short while, the system seemed to be okay. I’d lost some data because power cuts in January had encouraged me to disconnect my external back-up hard drive that seemed to be disturbed by the sudden, random loss of power! I’d forgotten to reconnect it. So, I lost the data (written work and a whole load of photographs) that hadn’t been backed-up.

When I say the system appeared to work for a short time, I mean for around an hour. After that, it slowed down and eventually stopped. I repeated the ‘safe mode’ deletion and re-installation, and, again, the machine seemed to operate reasonably. However, after a few days, another update was flagged, and always a believer in keeping things up to date, I let it run.

Guess what?

The same problem as before, with the loop of unhelpful information from which there appeared to be no escape.

By this time, I was getting a little fed up. I searched online, in safe mode, for help. I was directed to a site that offered what appeared to be a solution without charge. Unconvinced, but by now desperate to get back to work on the current novel, I downloaded the software only to be informed that the machine had around 368 issues. They could be solved, if I paid for the software. This, of course, is the expected result. I checked out the company and their software online through the usual channels and discovered they’re well-respected.

The software cost me about £110.00 but I installed and ran it and it appeared to do the trick. For a while.

Again, the machine simply slowed down and then hung after around an hour of use.

One feature of the software program was the opportunity to ‘ask an expert’, again, this seemed at first sight to be free. With some trepidation, I followed the online instructions and began a ‘chat’ with one of the operatives. He guided me through some options and spent a fair time with me, but we found no solution. It seemed we’d need to go to a specialist. I asked about the price for this and he advised me there were several options, pointing me in the direction of the offers.

The cheapest shown was £354.00 for a 6 month contract including a monthly service of the Mac. (I never knew computers required regular servicing, did you?). It was out of my league, and I explained this. He consulted his supervisor who said they would do a one-off deal at £140.00. Still too high a price for me. I could return to the local expert and get the job done for £90.00. They offered me the service for £88.00. I took that, since it would save me the travel time and expense and meant the machine remained at home.

Then began the real saga. The first techie took over the machine, with my permission, and spent a long time seeking the root of the problem. I was required to be on hand during parts of this process and, after midnight on the first day, he said he’d found and cured the problem and would now restore my data overnight. I could leave him to it.

The following day, around lunch time, the process had completed and I began to use the machine again.

Guess what?

That’s right. It lasted around an hour, again.

I called up the techies and explained. The advice was to restart in ‘safe mode’ and a new techie would make further investigations once I could connect him. I won’t go into great detail here, but, after 5 techies and 3 days of ‘help’ (at no extra cost, I must add), the final solution was a ‘clean reinstall’, which involved downloading the OS onto another external hard drive (fortunately I had a spare, unused) and then installation from that to the Mac. On each of the days, I was up until gone midnight to provide onsite support when required.

The machine was finally fixed and I thanked the various techies and settled down to do some work.

Guess what?


Same story.


By now, I didn’t care what happened to the Mac. It was more trouble than it was worth. I decided I could no longer continue with this situation and went online via my wife’s laptop to find and buy a Windows machine.

John Lewis came up with the best offer for the sort of thing I wanted and I looked forward to receiving my new Dell machine within a couple of days.

Not the end of the story.

My payment had been refused, said a nice lady on the phone from John Lewis. This was a little alarming, as I knew the account held more than enough to cover the purchase. It turned out that the ‘unusual’ spending had triggered the bank’s security system and they’d frozen the account pending my contact, in case someone else had got hold of my bank card! A brief phone call and a lot of questions and answers later, the payment went through.

My new Dell arrived on 28th February. Thus almost the entire month of February had proved a waste of time as far as writing was concerned.

And then the fun began. I’d lost some software, of course. This included MS Office, the 2011 version. When I tried to reinstall this, I was asked for a verification number, which I don’t have, as the Mac came with the software installed and no disc. I chatted with my brother, as I recalled he’d solved a similar problem some years ago. He reminded me about the potential of an MS account, which might hold details. I couldn’t find one. So I opened one and contacted MS about the issue. To cut a long story short, after learning of my issues, they provided me with a free year’s account using MS 365 and providing me with the 2016 Office Suite.

I installed that on the Dell. But I’d also lost Lightroom software, which I used as both a catalogue for my photos and as editing software. Lightroom 5 is no longer available and Adobe seem to have problems with Lightroom 6 as a one-off download, judging by the many adverse comments online. So I decided to give it a miss and use a free photo editing suite instead.

I attached my external hard drive to recover my data and pics from there. And that’s when I discovered something I hadn’t expected. The drive was formatted for the Mac, which made it unreadable by Windows.

Oh, good.

I did some online research and discovered a site that offered software designed to get over this problem. I was able to download a trial version, so I did. For reasons I don’t understand, and that the software didn’t explain, it didn’t work on my data. All the Office files came up as blank icons that Windows couldn’t access. I tried a few ways to get round this problem, but to no avail.

Next I did some more research and discovered my back-ups on iCloud should be capable of translation to Windows. But it wouldn’t be easy, or quick.

In short, the different operating systems prevent the recovery of data en masse. The only workaround for this is to access files manually. With the Office files, it’s possible to use Ctrl/select to gather a number of files and download these in one go. It’s slow, cumbersome and time-consuming, but at least the data can be recovered. Of course, every file is in a format that needs to be altered manually. What this means is that every single document has to be opened individually and then changed into a form that allows you to edit it, otherwise it remains as a ‘read only’ document. I’ve lost count of the number of documents I have in Office, but I know it exceeds 50,000. And each one will have to be opened manually and the change made. Fortunately, that involves clicking a button at the top of the document. But, I mean, tens of thousands of them? Individually?

Next came the pictures. I’ve been taking digital photographs for years. I used to be a professional photographer. When I looked at the ‘all photos’ file on iCloud, it listed 17,591 pictures there. I started the process of migration to my Dell. After some experimentation, I found I could collect a number of picture files at a time, using Ctrl/select, as with the docs. I can then download these to my ‘Pictures’ file on the Dell. The default destination is the ‘Downloads’ folder, but I didn’t want to have to move them all from that folder to the ‘Pictures’ folder. After a little messing around I discovered I could download direct into the ‘Pictures’ folder. But the whole process is cumbersome, slow and time-consuming.

The best bet was to reduce the number of pictures I needed to transfer, so I went through the whole collection and reduced the count from 17,591 to 13,493. That took the best part of a day!

I then discovered that collecting too many files at any one time caused more problems than it solved, slowing the whole process down radically. I settled on transferring 20 files at a time and can now place these into any one of 14 folders I’ve already labelled. The problem stems from the fact that Macs don’t place photographs in folders, even if you, as the operator, use such a filing system, as I did with Lightroom. The Mac insists on grouping photographs by the date taken. Not helpful when my own filing system requires pictures to be organised along the lines of content rather than date!

So far, I’ve managed to recover the odd 493 pictures, a process that kept me at the computer for 3 hours. Even if I do 500 a day it’s going to keep me engaged for 26 days to complete the task. Oh, and in the meantime, iCloud regularly keeps trying to get me to ‘sign in’ so it can continue to act as a back-up for the files on my Windows machine. No way! I’ve reformatted the hard drive and am using that as a back-up. Once I’ve migrated all the data from iCloud, I intend to close that account and find a more friendly service on a cloud somewhere else, possible cloud 9, if I’m lucky!

Ah, the wonders of modern technology, eh?

So, if you’re thinking of changing your current Windows PC for a Mac, or changing your current Mac for a Windows PC, please be warned that the process is far from simple. Both operating systems exclude the other. There’s no concession to those who may have to, or choose to, use both systems. The companies involved appear to be much more concerned with making profits than with providing users with systems that are actually user-friendly. A sad example of the wonderful ‘American way’, it seems to me. But I’m now straying into contentious waters, and I don’t have spare time to engage in meaningful debate.

I’ve still got 13,000 individual pictures to import to my new PC, along with, at a guess, around 42,000 Office docs. Wish me luck. My patience, as you will no doubt appreciate, is wearing very thin!

14 thoughts on “Joys and Woes of #Windows-to-#Mac-to-Windows.

  1. Wow! I know how frustrating computer problems can be – especially transferring files, etc. I’ve always had a PC with Windows. At work, they gave us all an I-Pad. The Mac systems were so problematic and so incompatible with other office systems that we started calling them the I-Crap. I’ve never been impressed with Mac products. Good luck and smooth computing on your Dell 🙂

    Liked by 1 person

    1. Thanks, Stearley. I confess, I did like the Mac and it’s way of working, once I understood the thinking. It’s very different from Windows, so quite a steep learning curve. But I’m pleased to be back on Windows. Just spent another 2 hours migrating files: it’s a long and boring task, but I am finding stuff I’d forgotten about, some stories I’ve never published, so there’ll be some pluses to this exercise in the end.

      Liked by 1 person

  2. Ye Gods, Stuart, that’s a saga and a half. I admit I do make sure everything is backed up regularly and I have no intention of changing my operating system because I just know it’s going to go wrong. Hope that’s the end of your problems.

    Liked by 1 person

    1. Thanks, Mick. Me, too! Managed to get another 500 pics migrated this morning. Back to restoring my docs for a while, now! So far, I’ve migrated about a tenth of those!

      Liked by 1 person

  3. I feel your pain. I got an imac in 2011 just to know how it works. It was a nightmare trying to get my Time Machine to work on my external hard drive that my husband and I gave up. (He works in the IT field by the way.) Fortunately the imac has held up till now. I’m not looking forward to the day I need to get a new computer though because I’m definitely going back to Windows to avoid any more compatibility issues. I have lots of photos and documents too.

    Liked by 1 person

    1. Good luck when you change, Eileen. I would seriously recommend, however, that you make the change BEFORE the Mac becomes unreliable: that way, you have a chance of migrating your files more easily from the working Mac to the new Windows machine.

      Liked by 1 person

    1. ‘I see a Bad Moon Arising…’ Somewhere, deep in the cellar above the haunted house, chains rattled as the spirit of persistence slowly dragged itself from the glooms of despair!


  4. My word!!! I can’t believe what an ordeal you’ve had. I’ve had my IMac for over 7 years with no glitches whatsoever. I hate to ask but were you in direct contact with Apple support? They should have been able to help you with these issues at no cost to you. Wishing you the best of luck with your new machine. There are plenty of cloud services out there, Google and Amazon are probably the best known. Again, hope it all gets sorted out!

    Liked by 1 person

    1. Thanks, Meg. It was Apple’s support section that suggested the first deletion and reinstallation of the OS. Since that didn’t work, I thought I’d try some independent support. I guess, by that time, I was suffering a surfeit of cynicism!
      On, now, with the task of getting everything working properly again, so I can do some proper work!

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