upgrade from lion to mountain lion failed

[aau]

I'm attempting to upgrade Mac OS X from 10.7 to 10.8 on my Late 2008/Early 2009 15" Macbook Pro. It's not working. If I perform an upgrade over 10.7 the Mac hangs upon first boot at the gray screen with an Apple logo and no progress wheel. I've left it alone for hours and it goes no further. If I perform a clean install, erasing the drive first, this works. But as soon as I import my Applications and my 10.7 User Account from a backup drive, it fails again with the same symptoms upon reboot. So something is being brought in from my old setup that is causing the failure. I can boot into 10.8 and login into my account in Safe Mode. What can I do from here to pinpoint the cause of my trouble? TIA

 

[Fishrrman]

I think you may have to do things slowly and surely to get where you want to go.

My suggestions:

You did say you have an external backup that has all your important files, correct?
(applications, accounts, data)

If so, I'd do this:
- Reinitialize the internal drive
- Install an absolutely clean copy of 10.8 onto it
- Reboot, go through initial setup sequence, and create a "dummy account" for now. That is, an account to get things running that is not intended to become your "main" account. Give it a name like "administrator" or something along that line.
- Get the administrator account up and running.
- Now, download all Apple software updates

At this point, you should have an up-to-date copy of 10.8.5 going.

Now, BEFORE you try migrating apps, do this:
- Use Migration Assistant, but be VERY SELECTIVE
- Choose to migrate ONLY accounts, settings, data
- DO NOT migrate apps yet.

Now, switch over from the administrator account to your old (real) account.
Reboot.
Can you get this far, without crashing?

At this point, I would consider re-installing 3rd-party apps -manually-, one-at-a-time. After each install, do a reboot, launch the app, open a data file or two, check things out carefully.
Then, install the next app.

Yep, I know this will be slow going.
You may need to keep a pad with handwritten notes.
But sometimes, that's the only way that works....

 

[Weaselboy]

So something is being brought in from my old setup that is causing the failure. I can boot into 10.8 and login into my account in Safe Mode. What can I do from here to pinpoint the cause of my trouble? TIA

This is a big clue to the problem. Safe mode bypasses any login or startup items, so if it works in safe mode and not ion normal mode that tells you one of your startup or login items is causing the problem/conflict.

Run this Etrecheck utility and it will give you a list of all login and startup items so you can start eliminated them one by one to narrow down the culprit.

If you want, you can post the Etrecheck output here and we can maybe help you pinpoint common troublemakers.

 

[aau]

The weekend has finally provided me with more time to troubleshoot, and I've made great progress. My machine is running 10.8.5 now, after starting with a clean install, and migrating from a backup drive with a clone of the original 10.7 partition. I was able to migrate everything and reboot successfully, except for my Applications folder. I've been reinstalling apps and have everything but about a dozen apps restored. The programs still to go are not critical right now. I did download the Etrecheck utility an ran it on my 10.7 install, which I'm not booting into anymore but still have accessible. I have copied the output below. Thanks for any help isolating problematic files.

EtreCheck version: 1.9.15 (52)
Report generated September 12, 2014 9:36:46 AM PDT

Hardware Information: ?
MacBook Pro (15-inch, Late 2008) (Verified)
MacBook Pro - model: MacBookPro5,1
1 2.66 GHz Intel Core 2 Duo CPU: 2 cores
8 GB RAM

Video Information: ?
NVIDIA GeForce 9600M GT - VRAM: 512 MB
NVIDIA GeForce 9400M - VRAM: 256 MB
Color LCD 1440 x 900

System Software: ?
Mac OS X 10.7.5 (11G63) - Uptime: 0 days 0:3:40

Disk Information: ?
Samsung SSD 840 PRO Series disk0 : (256.06 GB)
S.M.A.R.T. Status: Verified
disk0s1 (disk0s1) <not mounted>: 209.7 MB
Samsung SSD (disk0s2) /Volumes/Samsung SSD: 255.2 GB (105.88 GB free)
Recovery HD (disk0s3) <not mounted>: 650 MB

OCZ-AGILITY4 disk1 : (128.04 GB)
S.M.A.R.T. Status: Verified
disk1s1 (disk1s1) <not mounted>: 209.7 MB
OCZ SSD (disk1s2) /Volumes/OCZ SSD: 127.04 GB (19.43 GB free)
Recovery HD (disk1s3) <not mounted>: 650 MB

USB Information: ?
Apple Inc. Built-in iSight
SanDisk Cruzer Fit 8 GB
S.M.A.R.T. Status: Verified
disk3s1 (disk3s1) <not mounted>: 209.7 MB
OS X Mountain Lion Install Disk - 10.8.2 (disk3s2) /Volumes/OS X Mountain Lion Install Disk - 10.8.2: 7.66 GB (3.2 GB free)
Apricorn SATAWire 320.07 GB
S.M.A.R.T. Status: Verified
disk2s1 (disk2s1) <not mounted>: 209.7 MB
Macintosh HD10.6 (disk2s2) /Volumes/Macintosh HD10.6: 82.4 GB (1.47 GB free)
Macintosh HD10.7 (disk2s3) / [Startup]: 237.19 GB (35.31 GB free)
Apple, Inc. Apple Internal Keyboard / Trackpad
Apple Computer, Inc. IR Receiver
Apple Inc. BRCM2046 Hub
Apple Inc. Bluetooth USB Host Controller

Firewire Information: ?
G-TECH OEM ATA Device 00 800mbit - 800mbit max
S.M.A.R.T. Status: Verified
disk4s1 (disk4s1) <not mounted>: 209.7 MB
G-DRIVE Mini (disk4s2) /Volumes/G-DRIVE Mini: 213 GB (3.12 GB free)
Recovery HD (disk4s3) <not mounted>: 650 MB
MacOSXSrv10.5.8 (disk4s4) /Volumes/MacOSXSrv10.5.8: 118 GB (22.51 GB free)
MacOSX10.8 (disk4s5) /Volumes/MacOSX10.8: 24.17 GB (8.72 GB free)
Recovery HD (disk4s6) <not mounted>: 650 MB
MacOSXSrv10.6.8 (disk4s7) /Volumes/MacOSXSrv10.6.8: 106.14 GB (16.54 GB free)
MacOSXSrv10.4.11 (disk4s8) /Volumes/MacOSXSrv10.4.11: 36.88 GB (22.06 GB free)
disk4s9 (disk4s9) <not mounted>: 134.2 MB

Configuration files: ?
/etc/hosts - Count: 1

Kernel Extensions: ?
[not loaded] com.getgreenbytes.driver.zfs (2012.09.14 - SDK 10.6) Support
[not loaded] com.getgreenbytes.filesystem.zfs (2012.09.23 - SDK 10.6) Support
[not loaded] com.microsoft.driver.MicrosoftMouse (8.2) Support
[not loaded] com.microsoft.driver.MicrosoftMouseBluetooth (8.2) Support
[not loaded] com.microsoft.driver.MicrosoftMouseUSB (8.2) Support
[loaded] com.paragon-software.snapshot.kext (2.0.0 - SDK 10.5) Support
[not loaded] com.wdc.driver.1394HP (1.0.9) Support
[not loaded] com.wdc.driver.1394_64HP (1.0.1 - SDK 10.6) Support
[not loaded] com.wdc.driver.USBHP (1.0.11) Support
[not loaded] com.wdc.driver.USB_64HP (1.0.0 - SDK 10.6) Support
[loaded] org.virtualbox.kext.VBoxDrv (4.3.14) Support
[loaded] org.virtualbox.kext.VBoxNetAdp (4.3.14) Support
[loaded] org.virtualbox.kext.VBoxNetFlt (4.3.14) Support
[loaded] org.virtualbox.kext.VBoxUSB (4.3.14) Support

Startup Items: ?
IcebergControlTower: Path: /Library/StartupItems/IcebergControlTower
MySQLCOM: Path: /Library/StartupItems/MySQLCOM
SteelVineDaemon: Path: /Library/StartupItems/SteelVineDaemon

Launch Daemons: ?
[loaded] com.adobe.fpsaud.plist Support
[loaded] com.adobe.SwitchBoard.plist Support
[loaded] com.atlassian.SourceTreePrivilegedHelper2.plist Support
[loaded] com.barebones.authd.plist Support
[loaded] com.barebones.textwrangler.plist Support
[loaded] com.bombich.ccc.plist Support
[not loaded] com.deploystudio.server.plist Support
[loaded] com.getgreenbytes.zfs.delegate.plist Support
[running] com.getgreenbytes.zfs.loader.plist Support
[loaded] com.github.GitHub.GHInstallCLI.plist Support
[loaded] com.intego.commonservices.metrics.kschecker.plist Support
[loaded] com.microsoft.office.licensing.helper.plist Support
[loaded] com.oracle.java.Helper-Tool.plist Support
[loaded] com.oracle.java.JavaUpdateHelper.plist Support
[running] com.paragon-software.snapshot.daemon.plist Support
[loaded] com.skype.skypeinstaller.plist Support
[loaded] org.cindori.AuthHelper.plist Support
[running] org.macports.sleepwatcher.plist Support
[not loaded] org.virtualbox.startup.plist Support

Launch Agents: ?
[not loaded] com.adobe.AAM.Updater-1.0.plist Support
[loaded] com.getgreenbytes.zfs.notifier.plist Support
[loaded] com.oracle.java.Java-Updater.plist Support

User Launch Agents: ?
[loaded] com.adobe.AAM.Updater-1.0.plist Support
[loaded] com.adobe.ARM.[...].plist Support
[loaded] com.adobe.ARM.[...].plist Support
[running] com.amazon.cloud-player.plist Support
[loaded] com.divx.agent.postinstall.plist Support
[loaded] com.google.keystone.agent.plist Support
[loaded] com.valvesoftware.steamclean.plist Support
[not loaded] org.virtualbox.vboxwebsrv.plist Support

User Login Items: ?
Box Sync
iTunesHelper
GeekTool Helper
MicrosoftMouseHelper
Amazon Cloud Drive
Dropbox
GrowlLauncher
IceFloor Menulet
VMware Fusion Helper
BoxSyncHelper

Internet Plug-ins: ?
AdobeExManDetect: Version: AdobeExManDetect 1.1.0.0 - SDK 10.7 Support
Flip4Mac WMV Plugin: Version: 3.2.0.16 - SDK 10.8 Support
AmazonMP3DownloaderPlugin101750: Version: AmazonMP3DownloaderPlugin 1.0.17 - SDK 10.4 Support
AdobePDFViewerNPAPI: Version: 11.0.07 - SDK 10.6 Support
FlashPlayer-10.6: Version: 15.0.0.152 - SDK 10.6 Support
Silverlight: Version: 5.1.30514.0 - SDK 10.6 Support
Flash Player: Version: 15.0.0.152 - SDK 10.6 Support
QuickTime Plugin: Version: 7.7.1
AmazonMP3DownloaderPlugin: Version: AmazonMP3DownloaderPlugin 1.0.17 - SDK 10.4 Support
SharePointBrowserPlugin: Version: 14.4.4 - SDK 10.6 Support
AdobePDFViewer: Version: 11.0.07 - SDK 10.6 Support
QualysBrowserCheckSafari: Version: 1.0.48.1 - SDK 10.7
JavaAppletPlugin: Version: Java 8 Update 20 Check version

Safari Extensions: ?
OpenIE
ClickToPlugin-2
ClickToFlash-2

Audio Plug-ins: ?
iSightAudio: Version: 7.7.1 - SDK 10.7

iTunes Plug-ins: ?
Quartz Composer Visualizer: Version: 1.3 - SDK 10.7

3rd Party Preference Panes: ?
DeployStudioServer Support
Flash Player Support
Flip4Mac WMV Support
Java Support
Microsoft Mouse Support
MySQL Support
Perian Support
ZEVO Community Preferences Support

Time Machine: ?
Time Machine not configured!

Top Processes by CPU: ?
28% lsregister
19% coreservicesd
2% WindowServer
0% Dropbox
0% fontd

Top Processes by Memory: ?
90 MB Box Sync
90 MB mds
66 MB Dropbox
57 MB Dock
49 MB Amazon Cloud Drive Sync Service

Virtual Memory Information: ?
5.99 GB Free RAM
878 MB Active RAM
317 MB Inactive RAM
603 MB Wired RAM
327 MB Page-ins
0 B Page-outs

 

[Weaselboy]

Thanks for any help isolating problematic files.


Kernel Extensions: ?
[not loaded] com.getgreenbytes.driver.zfs (2012.09.14 - SDK 10.6) Support
[not loaded] com.getgreenbytes.filesystem.zfs (2012.09.23 - SDK 10.6) Support
[not loaded] com.microsoft.driver.MicrosoftMouse (8.2) Support
[not loaded] com.microsoft.driver.MicrosoftMouseBluetooth (8.2) Support
[not loaded] com.microsoft.driver.MicrosoftMouseUSB (8.2) Support
[loaded] com.paragon-software.snapshot.kext (2.0.0 - SDK 10.5) Support
[not loaded] com.wdc.driver.1394HP (1.0.9) Support
[not loaded] com.wdc.driver.1394_64HP (1.0.1 - SDK 10.6) Support
[not loaded] com.wdc.driver.USBHP (1.0.11) Support
[not loaded] com.wdc.driver.USB_64HP (1.0.0 - SDK 10.6) Support
[loaded] org.virtualbox.kext.VBoxDrv (4.3.14) Support
[loaded] org.virtualbox.kext.VBoxNetAdp (4.3.14) Support
[loaded] org.virtualbox.kext.VBoxNetFlt (4.3.14) Support
[loaded] org.virtualbox.kext.VBoxUSB (4.3.14) Support

Startup Items: ?
IcebergControlTower: Path: /Library/StartupItems/IcebergControlTower
MySQLCOM: Path: /Library/StartupItems/MySQLCOM
SteelVineDaemon: Path: /Library/StartupItems/SteelVineDaemon

Launch Daemons: ?
[loaded] com.adobe.fpsaud.plist Support
[loaded] com.adobe.SwitchBoard.plist Support
[loaded] com.atlassian.SourceTreePrivilegedHelper2.plist Support
[loaded] com.barebones.authd.plist Support
[loaded] com.barebones.textwrangler.plist Support
[loaded] com.bombich.ccc.plist Support
[not loaded] com.deploystudio.server.plist Support
[loaded] com.getgreenbytes.zfs.delegate.plist Support
[running] com.getgreenbytes.zfs.loader.plist Support
[loaded] com.github.GitHub.GHInstallCLI.plist Support
[loaded] com.intego.commonservices.metrics.kschecker.plist Support
[loaded] com.microsoft.office.licensing.helper.plist Support
[loaded] com.oracle.java.Helper-Tool.plist Support
[loaded] com.oracle.java.JavaUpdateHelper.plist Support
[running] com.paragon-software.snapshot.daemon.plist Support
[loaded] com.skype.skypeinstaller.plist Support
[loaded] org.cindori.AuthHelper.plist Support
[running] org.macports.sleepwatcher.plist Support
[not loaded] org.virtualbox.startup.plist Support

Launch Agents: ?
[not loaded] com.adobe.AAM.Updater-1.0.plist Support
[loaded] com.getgreenbytes.zfs.notifier.plist Support
[loaded] com.oracle.java.Java-Updater.plist Support

User Launch Agents: ?
[loaded] com.adobe.AAM.Updater-1.0.plist Support
[loaded] com.adobe.ARM.[...].plist Support
[loaded] com.adobe.ARM.[...].plist Support
[running] com.amazon.cloud-player.plist Support
[loaded] com.divx.agent.postinstall.plist Support
[loaded] com.google.keystone.agent.plist Support
[loaded] com.valvesoftware.steamclean.plist Support
[not loaded] org.virtualbox.vboxwebsrv.plist Support

Good deal... sounds like you are narrowing it down and one of the startup login items if the culprit (you have a lot! ). I would start with the third party items I bolded, particularly that ZFS driver.