I have a Macbook Pro with OS X 10.8.5 currently installed. I have the corresponding Xcode as 5.1. Now In order to use Swift we need Xcode 6 and above which is only available for OSX 10.9 or later.

My question:

I had to upgrade my OS sooner or later even if I was not using Swift. My concern are: 1).I have lots of softwares installed on my current Macbook. Like I have Anaconda Python Distribution package. Similarly I have R studio , IDLE (Python 3.3) using Homebrew Package Manager etc. When I click on the online upgrade to Yosemite, will I lose all the existing softwares installed on my current OS?. What about other files?

2). Also in case I don't lose my existing softwares, will the existing softwares stop working especially like Anaconda etc due to some compatibility conflict?

I think I would have to upgrade to new OS which is Yosemite currently but I am very sceptical if this would make me lose my current set of softwares and files or make them incompatible with others? Some of those softwares installation is really a big pain like installing new Python using Homebrew along with other lib.

Please advise.



I can't directly answer your specific questions but I advise you to wait before upgrading. Right now version 10.0.1 is out and I still have a couple problems I never had on Mavericks (now imagine all issues you'll have coming from 10.8). But as far as I remember from upgrading to Mavericks a year ago, I didn't lose any software or packages nor did I have any problems.

  • Hi do you suggest upgrading now? is it stable? – Baktaawar May 25 '15 at 1:27

Your existing software will remain in place. When upgrading your OSX installation from 10.8.5 to 10.10 it will not wipe your drive and you will not loose your current set of applications and files. The question of compatibility is however a separate issue.

Regarding homebrew, there apparently was an issue with homebrew on Yosemite since the default version of ruby was upgraded to 2.00 on Yosemite. The issue has recently been closed so I suspect if you are running the latest update of homebrew it will continue working . Otherwise instructions on how to get it up and running again can be found in the following answer. The neat thing about homebrew is that everything is installed separately in /usr/local, so it does not conflict with shipped tools from Apple. My python3 installation from homebrew continues to work beautifully alongside the apple shipped version of python on Yosemite.

Apparently I can't find any information about Anaconda and Yosemite compatibility. A new version hasn't been posted since 09/30 and the changelog never even mentions about a fix/enhancement for yosemite.

A special note about updating to Yosemite. I reckon that you have a lot of additional applications, libraries and files installed through homebrew or separate installers. During the installation your main drive (hdd/sdd) will be converted from a regular HFS+ Volume to a CoreStorage Logical Volume Group (more info at Arstechnica) which depending of the number of files can't take anywhere between 5 minutes and a couple of hours. It might look like the setup is stuck at" One minute remaining" but if you open up the installer log using the shortcutCommand + L you can see the installer moving your files. So don't worry about the setup being stuck and just wait it out (took about an hour on a 512GB SSD drive).

  • Hi Sorry for late comment. Just wanted to know. Should I back up my drive. I have a Macbook Pro with 750GB drive. I have used only 95GB until now. So how much do you think it might take if I do online upgrade to Yosemite from App store? – Baktaawar May 25 '15 at 1:27

You must log in to answer this question.

Not the answer you're looking for? Browse other questions tagged .