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SideKick was an early , and its window-based interface echoed (in text format) that of the Apple Macintosh , and anticipated the eventual look of Microsoft Windows 2.0 . It featured a personal calendar, text editor (with WordStar -like command interface), calculator, ASCII chart, and address book/phone dialer.

A version was also available for the early models of the Apple Macintosh.
The software and tradename were sold to Starfish Software , a division of Motorola . Starfish was later bought by PumaTech (now Intellisync ), who discontinued the product, with SideKick 99 being the last version.

Later versions of the program were made available for Windows, and were more along the lines of Microsoft Outlook , with the last versions of it supporting such features as a phone dialer, and support for syncing with Palm , Windows CE , and EPOC devices. These versions were less popular than the DOS versions, largely because the Windows environment itself provided most of the original version's key features: task switching and a collection of small utilities. It did however, include a monthly/yearly calendar and a world time map showing which parts of the world are currently in daylight or darkness. Up to eight different world cities (which could be edited) were displayed above and below the map.

There may be an error message while trying to install Sidekick 99 on Windows XP. The installer incorrectly notifies the user that another instance of the program is running, when in fact it is being installed for the first time. This can be fixed be renaming a file in the Windows directory (top level) called ''wininit.ini'' to ''wininit.old'' (or some other name).