When I plug my phone into any pc I don't get prompted to enable mass storage mode. This seems to work fine on my wives phone. We both have Nexus S's and were both running 2.3.2 but I manually upgraded to 2.3.3 hoping that would correct the issue but it didn't help.
You know what's weird is i have this exact same problem. When i connect my fiancee' Nexus S it automatically prompts to turn on USB storage. But when i plug in my Nexus S is doesn't prompt me automatically and i manually have to do it. There has to be a setting to change this but i haven't found it. It did this to me on stock 2.3.2 and is still doing it on CM7 RC1.
If anyone knows a fix to this i would love to find out.
I had the same problem with my Nexus S and 1st Generation MacBook Air. I was using a generic USB cable. I just switched it out for the cable that came with the phone and now it is finally prompting me for mass storage mode.
go to "settings" --> "SD card & phone storage" --> then uncheck "mass storage only" then put the check back in. You should now get the option on your phone to "Turn on USB Storage" Hope that helps even tho its a little late
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