Need to update OS High Sierra to Catalina For TurboTax

[JoeMcCaz]

PREFACE:
My Mac, which I purchased almost 10 years ago, works awesome. Unfortunately last tax year (2020) when I purchased the TurboTax (TT) CD I found my OS wouldn't work it. Called TT and they said best bet is to do taxes online. They gave me a code to use after I was done that would allow me to file for free (since I already bought the CD) both state and federal, great right? Well I started and life got crazy, I filed for an extension, first time in my working life (approx 50 years) I ever didn't have taxes filed by end of Feb. Anyhow, I never got back to completing 2020 return and now it's time for 2021. I tried to get in and finish my 2020 return but found the online is closed and the only way I can complete is to have TT download for me and I know my OS won't work it.

QUESTIONS:
1- Can I upgrade to Catalina without screwing up everything I have on my machine? IE: Office for Mac, pictures, files, years and years of things I can't imagine loosing? Yes, I need to do a backup to my external drive for sure...
2- What am I to expect if I upgrade?
3- Will it take forever?
4- Could there be a terminal failure that'll totally screw the pooch?

Now that life isn't as crazy as it was in 2021 I really need to get my 2020 return filed and suffer the consequences of filing so late. Then I can get back on track to my typical "Get the (2021) return done and filed immediately".

Thanks,

Joe

 

[chscag]

Keep in mind that updating to Catalina from High Sierra will cause all your 32 bit apps to not function. macOS Mojave is the last version to support 32 bit apps.

Also, if you have not already formatted your drive to APFS, it will automatically be done in Catalina.

Those are things you need to consider.

I have no experience lately with TurboTax as I use the H.R. Block software. However, I have never been a fan of doing my taxes on line, free or not.

 

[pigoo3]

My Mac, which I purchased almost 10 years ago, works awesome.

1- Can I upgrade to Catalina without screwing up everything I have on my machine?

Hello Joe. My wife & I were in the exact same position this year (needed to upgrade macOS to run this years version of Turbo Tax)...certainly understand your position.

First & foremost...if your Apple computer we're talking about was purchased almost 10 years ago...it may or may not be able to run macOS Catalina.

To be 100% sure...please provide the exact spec's of the computer...and we can verify. In case you're not sure where to find this info...go to:

Apple drop down menu >> About This Mac

Once we have verified if the computer can or cannot run Catalina...we can proceed. If it can run Catalina...can suggest a fairly easy solution.

Nick

 

[Raz0rEdge]

Your 2013 iMac is compatible with Catalina but keeping in mind everything that's been stated about how big of a jump this is from High Sierra, you might want to proceed with caution.

You can grab a copy of Catalina from the App Store.

‎macOS Catalina

‎macOS Catalina gives you more of everything you love about Mac. Experience three all-new media apps: Apple Music, Apple TV, and Apple Podcasts. Locate a missing Mac with the new Find My app. And now coming to Mac, your favorite iPad apps. You can even extend your desktop using iPad as a second...

apps.apple.com

 

[pigoo3]

If we're talking a 2013 iMac (as Raz0rEdge mentioned it's compatible with Catalina)...AND...you do not want to run into any issues with what you have currently installed & running fine with macOS High Sierra...then the solution I did with my wife's MacBook Air was create a dual boot setup.

Dual boot means you retain everything as it is now (macOS High Sierra install)...then create a new partition for the Catalina install & new Turbo Tax install. These are separate entities...each needs to be booted into depending on what you want to do (boot into the High Sierra install for your normal computing...boot into the Catalina install to do Turbo Tax stuff).

Here's an Apple document that explains how to do things:

Partition a physical disk using Disk Utility on Mac

In Disk Utility on your Mac, partition a storage device into several partitions, each of which acts as a separate volume.

support.apple.com

The most important first step in this procedure (as can be seen in the Apple document)...it verifying how your computer's internal storage is formatted ("macOS Extended Journaled" or "APFS")...then follow the appropriate procedure in the Apple document.

Nick

 

[JoeMcCaz]

Chscag, I greatly appreciate your reply. I'm not very savvy with macs and computers, but I can tear a transmission (standard-remember them, or automatic), engine (gas or diesel), carburetor, injectors, pumps, differential apart figure what's wrong and usually get it going. Sort of like you guys with macs and computers. That said, I have no idea what a 32 bit app is, or formatting my drive to APFS (whatever that is)? I do know what valve seats, cam bearings, rings, sprags, nozzles, vanes, torque converters, ring and pinions are though. And, no I didn't stay in a Holiday Inn last night.

Not being a wise arse by any means, just letting everyone know what they're dealing with relative to me and my knowledge of macs and computers. At one time I was pretty darned good with figuring out things with computers but that was long ago when DOS (remember that?) was the thing. Since about 2000 I let the wave of technology crash me into a shore of sea shells and became satisfied to just know/figure out how to operate (best as I can) macs or computers. I am what I am and not a bit ashamed of it, too old to give a hoot what others think of me, not my problem. Right.

pigoo3, I greatly appreciate your replies as well. And that you were in the same position as I.
1st reply
As requested.

I seem to recall sometime after we purchased we update the OS to Snow Leopard and something else before HS, not sure if that matters. I didn't like the idea one bit of doing my taxes on line either but I was stuck with the situation at the time. Previously I'd take the machine offline do my taxes, print and mail them. Transfer the return to an external drive, delete from the machine then go back on line.
2nd reply
Regarding the link you provided, I took a quick look and made a bookmark to get back to it. First glance to me, looks like brain surgery. I get what you're saying though, sort of like splitting one brain into two within the same head. Makes sense in theory but like I said, to me it seems like brain surgery. I'll take a look at the bookmark sometime over the next few days. I'm on the homeward stretch of a little renovation project involving hot water and laundry room, so right now my priority is a hot shower and being able to clean cloths in my home.

Raz0rEdge
Thanks for your reply. I have no idea what's been stated about how big of a jump Catilina is from High Sierra. I am pleased with how my mac runs on HS and very frightened of updating the OS to something that'll crash me into the "technological shell ridden beach".

Time to grout the tile floor, catch you all later.

Thanks all and I appreciate any future replies,

Joe

 

[chscag]

Hi Joe:

As I stated in my first reply, you can update to Catalina (that's as far as you can go) but the move to Catalina will stop all 32 bit apps that you have from running.

That means older versions of MS Office, iWork apps, and many others that are 32 bit versions will not run at all. That is something you need to consider.

Okay, how can you determine which applications are 32 bit? From the same screen shot you sent us above, click on "System Report". Then scroll on down to "Software, Applications". Click on "Applications" and give it time to fill up. Then look over the last column which will identify whether the application is 32 bit or 64 bit.

After that you may be able to make a more informed decision on whether or not to update to Catalina.

You don't want to run out of gas on i15 on the way to Las Vegas... And you certainly don't want to run out of gas dealing with the IRS.

I'm not fond of dealing with Intuit but I'm sure they can accommodate you with something to allow you to do your taxes on line by providing access to your stored data.

Keep us posted. And if we can be of more help, let us know.

 

[IWT]

@JoeMcCaz

Your reference to brain surgery can be used as a model for what is being suggested. The brain has two halves - hemispheres.

In computer terms, we are suggesting that you separate the two hemispheres. Keep one for your current Operating System (OS) and use the other, when required, for Catalina.

Although the two hemispheres are contained within the skull, ie the Mac, they would now work separately, each having no knowledge of the other's existence. They would each share same the blood supply - electric power - and when one was was selected for use, the other would lie quietly dormant until activated.

This is the basis of a partition. Each works independently when selected. The one NOT in use would lie dormant until it was required.

The selection process is called booting. You boot into the one you need. Later you exit that one and boot into the other.
Now you see how easy brain surgery is

Good luck.

Ian

 

[hempomatic]

Personally, I wouldn't even consider updating past Mojave, which for ME was the last OS that I found trouble free. Catalina has been a complete and total disaster on so many levels, the list is endless. I'm talking about an UPGRADE to Catalina. The newer computer that had Catalina pre-installed runs fine, but I will NEVER again upgrade any Mac computer if there is ANY way I can avoid it ........ EVER!

An upgrade from High Sierra to Catalina is a profound change, not an incremental one. There is not a single program that I used before upgrading from Mojave ( all Apple programs btw) that still work. That includes my CD player/burner which I need to RE-record the thousand CDs that the "Upgrade" to MUSIC from iTunes decided to delete.

My recommendation, if you can do your taxes ANY other way .......... unless of course you don't need ANYTHING presently on your computer. Just one guy's opinion, and I'm sure a VERY unpopular one here.

 

[Raz0rEdge]

This is one of the PRIMARY reasons that people should look at each OS upgrade when it is released and upgrade to it if there is nothing that is going to break. Doing so means that you learn about the changes in an incremental fashion and can figure out how to adapt your workflow, if needed.

I've upgraded my macs to the newest OS available very quickly after it is released and have switched to use whatever new has become available and have had zero issues with my systems.

Yes, jumping from High Sierra to Catalina is huge since a lot of things have changed over the time, but jumping from Sierra to High Sierra and High Sierra to Mojave was no biggie.

 

[hempomatic]

Yes, jumping from High Sierra to Catalina is huge since a lot of things have changed over the time, but jumping from Sierra to High Sierra and High Sierra to Mojave was no biggie.

Mojave to Catalina is pretty huge. My old computer started with Mavericks, ended up with Mojave before the wheels came off. Mojave had a few things I didn't need or care for for, but Catalina is on a different planet.

 

[toMACsh]

This is one of the PRIMARY reasons that people should look at each OS upgrade when it is released and upgrade to it if there is nothing that is going to break. Doing so means that you learn about the changes in an incremental fashion and can figure out how to adapt your workflow, if needed.

Well, yeah, that's why I'm still on Mojave. But then I still do my taxes with a pencil (first) and pen (final to submit) and a calculator.

I should probably switch to using a computer, as my pencil still misspells words.

 

[MacInWin]

What about leaving your internal drive just as it is and getting an external drive, install what you need on it, boot from it and run Turbotax there to do your taxes and then going back to your old internal drive. That way there is no need to worry about compatibilities and upgrades. Then, in slower time, you can make an informed decision of whether to upgrade the internal drive or not. Running from an external will be slow, due to the USB interface, but probably workable for TT.

 

[rbpeirce]

I had a similar problem. 2021 TurboTax required 64-bit. Unfortunately I still have 32-bit software I need to keep running. My MBP was a 2012 so I decided it was old enough to replace. I was able to use Migration Assistant to transfer just about everything. I also had backups and my old computer for anything that got missed. I think that was one or two apps.

The only immediate downside was my Time Machine drive was not APFS so I had to reformat it and start over. Everything else worked fine.

The 2012 MBP is currently being used just to run the 32-bit apps.

 

[ferrarr]

What about leaving your internal drive just as it is and getting an external drive, install what you need on it, boot from it and run Turbotax there to do your taxes and then going back to your old internal drive.

This would be my suggestion as well. Works great. Plug is as needed.

 

[rbpeirce]

What about leaving your internal drive just as it is and getting an external drive, install what you need on it, boot from it and run Turbotax there to do your taxes and then going back to your old internal drive. That way there is no need to worry about compatibilities and upgrades. Then, in slower time, you can make an informed decision of whether to upgrade the internal drive or not. Running from an external will be slow, due to the USB interface, but probably workable for TT.

I missed this before. I did that but haven't needed it. I put an SSD in a box and installed everything I needed on it. It was pretty cheap. I never used it because I either had to run it or the upgraded system and I wanted to be able to run both at the same time so I ended up buying a new computer. However, this would certainly be a great idea if you can run one or the other.

 

[rbpeirce]

This would be my suggestion as well. Works great. Plug is as needed.

-- Bob--
Please backup. Every thing has a life cycle, unexpected and warning free. Nothing will last as long as you want it to.
PS: When there is an accident or error, is the tool to blame or is the fool to blame?


I do. I'm actually paranoid about it. I use Time Machine on the new computer and create an SD! sparsebundle on another drive each day on the new computer. I copy that sparsebundle to a RAID array once a week.

I'm less paranoid on the old machine because it never changes. However, I do back up its external data drive to the RAID array any time it changes.

I also have two RAID arrays, one in PA and one in VA. Chances are I won't lose anything but worst case it could be a couple of weeks.

 

[exncite]

PREFACE:
My Mac, which I purchased almost 10 years ago, works awesome. Unfortunately last tax year (2020) when I purchased the TurboTax (TT) CD I found my OS wouldn't work it. Called TT and they said best bet is to do taxes online. They gave me a code to use after I was done that would allow me to file for free (since I already bought the CD) both state and federal, great right? Well I started and life got crazy, I filed for an extension, first time in my working life (approx 50 years) I ever didn't have taxes filed by end of Feb. Anyhow, I never got back to completing 2020 return and now it's time for 2021. I tried to get in and finish my 2020 return but found the online is closed and the only way I can complete is to have TT download for me and I know my OS won't work it.

QUESTIONS:
1- Can I upgrade to Catalina without screwing up everything I have on my machine? IE: Office for Mac, pictures, files, years and years of things I can't imagine loosing? Yes, I need to do a backup to my external drive for sure...
2- What am I to expect if I upgrade?
3- Will it take forever?
4- Could there be a terminal failure that'll totally screw the pooch?

Now that life isn't as crazy as it was in 2021 I really need to get my 2020 return filed and suffer the consequences of filing so late. Then I can get back on track to my typical "Get the (2021) return done and filed immediately".

Thanks,

Joe

Have exactly the same issue. What I did was to create a separate volume and installed Monterey on it. When booting your computer, hold the Option key down and it will give you a choice of which volume to load.
Before you do that though, you’ll need to copy at least last year’s tax return onto the Monterey volume using Finder. That way, when you open Monterey (or at least Catalina if you so choose), TurboTax will be able to access the older returns. It won’t recognize them from your original volume.

That being said, I run Mojave which you might want to upgrade to. It works just fine. One of the other reasons I installed Monterey was to explore it. Have to say I’m disappointed with it and won’t upgrade my computer to have Monterey be the primary OS. Someday, a 64 bit OS will be necessary, but hopefully Apple will develop a better OS.

 

[IWT]

One of the other reasons I installed Monterey was to explore it. Have to say I’m disappointed with it and won’t upgrade my computer to have Monterey be the primary OS.

May I ask in what ways you were disappointed? Some of us here, myself included, tend to wait till there have been some updates to the original OS, in this case Monterey, before Upgrading from Big Sur. So any time now, a bunch of people will likely be upgrading.

Do you think that the big jump from macOS Mojave to Monterey was the real difficulty you had because there have been lots of changes through Catalina, Big Sur and now Monterey?

The overall impression I get from my fellow members is that Monterey is robust, fast and reliable.

Ian

 

[MacInWin]

Just to be clear, @exncite, by "volume" what do you mean? I ask because Apple now defines the structure of storage in terms of hardware, Partitions, Containers, and Volumes. So, for example, Monterey installation into a partition on a hardware drive creates two Volumes in the Container in which it is installed. I don't think Monterey can be installed into a Volume that exists under any other version of the OS. By using "volume" do you mean partition? That would be accurate, in that one could install Monterey into a separate Partition on the hardware with it's own Container and Volume(s). But re-partitioning an existing hard drive could lead to a loss of data on the existing drive, so it would need to be carefully done.