With Drupal 7 released (or about to be released) support for Drupal 5 is going to go away and to keep sites secure it is going to be imperative to upgrade to at least Drupal 6.

1. Water Torture Upgrades D5 to D6 Upgrade Click to insert horror stories here!

2. Familiar? River of Red

3. WorldFallz - November 29, 2009 - 07:19 Upgrading is definitely more complicated than it should be, but I wouldn't say 'extremely'. And the downside to staying with d5 is that it will be end of life as of the release of d7.

6. CCK and Views

7. Imagecache

9. 1. Update all modules to latest version. 2. Backup database. 3. Download all site files. 4. Disable/Uninstall Update Status Module. 5. Disable all contributed modules. 6. Switch to Garland theme. 7. Delete D5 files, saving sites, files and any extra folders or files I added. 8. Delete D5 contributed modules 9. Upload latest Drupal release files. 10. Upload D6 versions of contrib modules. 11. Go to /update.php and select continue then update. 12. Review update messages for significant errors. 13. Review modules and enable those compatible with D6. 14. Enable new (but optional) core update status module. 15. Check contributed theme status and update if necessary. 16. Re-save blocks and position. 17. Rebuild any previously built views. 18. Bring the site back online.

11. Prepare the site

12. Upgrade

13. Test site

14. Deploy

16. Contrib modules

17. CCK and Views

18. Custom Modules

20. Oh No More RED!

22. GUI (phpmyadmin)

24. Install Drupal 6, all contrib modules and theme.

26. Turn off contributed modules (do not uninstall)

27. Change theme to Garland or bluemarine

28. Set to maintenance mode

29. Login as user 1

30. Export database

31. Move it to your prepared D6 install

32. Run update.php

33. I loved your description! kappaluppa - November 28, 2009 – 08:46 Run update.php, get errors, enable a few more modules. Over and over and over.

34. More River of Red

37. Change variables

38. http://wtanaka.com/drupal/convert-theme-6

39. WSOD http://drupal.org/node/158043

41. CCK - http://drupal.org/node/822352

42. If all the CCK modules are in place..

43. Open the content type and pray

44. Start troubleshooting

45. Views -> Tools -> Convert

46. Fix as you go

47. http://drupal.org/node/822352

52. Convert a Drupal 5 theme to 6 ( http://wtanaka.com/drupal/convert-theme-6 )

53. Upgrading Drupal ( http://drupal.org/upgrade/ )

54. Converting 5.x themes to 6.x ( http://drupal.org/node/132442 )

55. Converting 5.x modules to 6.x ( http://drupal.org/node/114774 )

56. Acquia's take

57. http://acquia.com/documentation/getting-started/d5-migration/upgrade/testing/views