The import system for Season 1 saves may be tricky for some users, so here's a few helpful hints if you are having trouble importing your saves into Season 2.
How Do I Import My Save?
To import your Season 1 save, you will need to start Season 2 first. To do this, launch Season 2 and continue to the Main Menu. On the Main Menu, select 'Play', then 'Start Episode 1'. This will land you on a page asking if you want to import your Season 1 choices. Select 'Ok' to scan for completed Season 1 saves.
Complete Season 1 Episodes
Only completed Season 1 saves will be imported into Season 2. If you have any completed episodes, those choices will import to Season 2, and random choices will be made for any episodes that are unfinished or have not been played. If you've completed all episodes in the series, all your choices will be imported into Season 2.
Can't Find Season 1 Save?
Season 2 will look for a completed Season 1 save in the default save directory for Season 1. This directory is located in the C:\Users\%Username%\Documents\Telltale Games\The Walking Dead folder on PC, and ~Library/Application Support/Telltale Games on Mac. If these files have been moved or altered, or only the save files (and not the prefs.prop) have been kept, then Season 2 will not find your Season 1 save. Also, the Username determines where the saves are stored. If a different Windows account is being used to play Season 2, the saves for Season 1 will not be found.
Compatibility Mode/Windows 7 vs XP/98
Some users may have played Season 1 in Compatibility Mode on a Windows Vista or 7 computer. Windows Vista and 7 use the save directory C:\Users\%Username%\Documents\Telltale Games\The Walking Dead. All previous Windows OS, including XP and 98, use C:\Users\%Username%\My Documents\Telltale Games\The Walking Dead as the save directory. If Season 2 is unable to find your Season 1 saves, it may be looking in the wrong directory. Due to the way Windows creates new directories in Compatibility Mode, it's not possible to manually create this directory. The only way for Season 2 to see Season 1 saves is to play Season 2 in Compatibility Mode, as well.