Message: "Redownload Unavailable with This Apple ID"

[MacBook17]

We purchased our Early-2015 MacBook Pro 13 Retina Model from our area Apple store. As it has been used mostly for research and internet purchases for our small business, we've stuck with the operating system (OS) that it came with, Mac OS X 10.10 Yosemite.

We've recently run into issues completing purchases - from eBay for example - because of messages stating that our OS is too old. This being the case, I researched the internet for an OS update, but, unfortunately, after our Apple ID and Password are accepted, we get the following message ...

This message seems to indicate that Apple has flagged our machine as being of questionable origin. Does anyone know how to correct this issue?

Thank you very much for any help with this.

 

[Fishrrman]

The answer is that Yosemite is now too outdated to be able to work with some sites.

You need a newer version of the OS, and it may follow that you need a new (or new-ER) Mac on which to run it.

Hmmm...
Alternate course of action...
Get a small external SSD (256gb will do, get a 2.5" SATA SSD and an external USB3 enclosure to put it into)
Connect it to the 2015 MBP
Boot to INTERNET recovery (Command-OPTION-R at boot)
Open disk utility, go to the "view" menu and select "show all devices".
Erase the SSD to APFS (GUID partition format)
Open the OS installer, and then...
Install Monterey onto it (latest version of the OS the 2015 can use).
Set it up with an account for internet purchases.

Now if you can't reach sites using Yosemite, you can boot to Monterey from the external SSD, and probably get where you need to go that way.

 

[MacBook17]

Thank you for the advice.

Another question ... Is there a way to back up website bookmarks prior to updating the operating system?
The browsers in question are Safari and Chrome. Thank you.

 

[Fishrrman]

Safari --> File --> Export Bookmarks.

Probably similar for Chrome (but I wouldn't touch that with a 10-foot pole).

 

[macsound1]

This error message has nothing to do with your Mac, rather your Apple ID.

Apple allows any piece of software that was previously "purchased" (free or paid) to be downloaded in the future, even if it's not the most recent version.
The catch is you had to have "purchased" it before.
This error message is appearing when you want to upgrade to Yosemite because you hadn't "purchased" Yosemite when it was new, therefore Apple isn't allowing you to download it now.

This post has direct downloads to all the MacOS installer files. Just place the actual installer that's revealed after opening the dmg into your Application folder and double click. It'll install normally as an upgrade to your current OS.

How to Download MacOS Installers for New & Old Versions

Want to know how to download MacOS and Mac OS X installers? You might be wondering where you can download current and older versions of Mac OS from, particularly if you’re looking to update a…

osxdaily.com

Please do make a backup first, but all users, bookmarks, files, and history should remain intact.

 

[MacBook17]

Thank you, @macsound1, for the link and the words about why our MBP 13 Retina is behaving the way that it is.

My next question is whether or not it's safe to simply "skip over" operating system updates? In other words, is it safe to install macOS Monterey without installing the interim operating systems first? After all, OS X Yosemite began with version 10.10.X, while macOS Monterey began with version 12.6.X.

Many thanks for the help.

 

[Fishrrman]

Have you come to the decision that you want to replace the old OS (yosemite) with a new version (which should be Monterey) ??

If the answer is "yes"...
... then, do this.
PRINT OUT THIS REPLY AND SAVE IT FOR REFERENCE

1. BACK UP the MBP as it is now to an external USB3 drive.
2. For backing up, I recommend SuperDuper, which is FREE to use for this job. It's also very easy to understand. A few mouse clicks and the internal drive will be "cloned over" to the backup drive.
Get SuperDuper by clicking this link:
download

3. Once you've backed up, POWER OFF the MBP and DISCONNECT the backup.
4. Press AND HOLD this key combo (for internet recovery):
Command-OPTION-R, while you press the power on button.
KEEP HOLDING THOSE KEYS DOWN!

5. Let go when you are asked for your wifi password. Enter it.
6. Let the internet utilities load -- it will take a while.

7. When you get to the internet utilities, open disk utilty
8. VERY IMPORTANT STEP: go to the view menu and choose "show all devices"
(you can't see the internal SSD unless you do this!)

9. Look at "the list on the left". The topmost item should be the physical internal SSD.
10. Click on it ONE time to select it, then click "erase"
11. Erase to APFS (GUID partition format)
12. When the erase is done, quit disk utility.

13. Open the OS installer, and start "clicking through". The Mac will restart one or more times, and the screen may go dark for a minute or more with no other indications of activity. BE PATIENT.

14. When done, you should see the initial setup screen.
15. CONNECT YOUR BACKUP DRIVE NOW, and start clicking through.
16. Setup Assistant will ask if you wish to migrate from another drive. YES YOU DO.
17. "Point the way" for SA to the backup drive, and give SA time to "digest" everything.
18. I would migrate everything. Just let SA do its job, again, be patient.
19. When done you should see your old login screen, as before. So log in and "look around".

BE AWARE that some older 32 bit apps will no longer work. These will need to either be upgraded or replaced with something else.

Good luck.

 

[MacBook17]

I didn't get an answer about moving from the "native" OS, OS X Yosemite 10.10, to a much newer version of macOS, but Post No. 7 seems to indicate that it can be done.

I appreciate the procedure, @Fishrrman . I'm headed out to pick up the early-2015 MBP 13 Retina model in question later this evening. Once I have it, I'll bring it back to my home office and work on it personally. I'll be sure to get back with the results at some point after I attempt the upgrade.

Cheers!