This issue should be Mac specific.
There is an issue that affects Mac users who are using a "standard user account" under OSX. To correct this, log in to OSX under an "administrator account" and start LeapFrog Connect.
1. Open the "System Preferences" application.
2. Under "System," click "Accounts."
3. On the left side of the window, look for an account that has the word "Admin" displayed below it. Write down this account name.
4. Quit System Preferences.
5. At the top left of your screen, click the Apple icon in the Finder bar.
6. Select "Log Out".
7. At the OSX welcome screen, click the account name that you wrote down in step 3. Enter your OSX password for that account name.
8. Once the OSX desktop loads, start LeapFrog Connect.
You can now exit LeapFrog Connect and run it while using any of your OSX account names. You should no longer get unnecessary prompts to update LeapFrog Connect.