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Are you positive you are using outlook 99? MS says nothing about Outlook 99.
"Minimum Desktop Computer Requirements
Microsoft Windows XP, Windows 2000, Windows Millennium Edition, Windows NT Workstation 4.0 with SP6 or later, or Windows 98
Microsoft Outlook 98 or later required for synchronization to the desktop or portable computer of e-mail, calendar, contacts, tasks, and notes. (Outlook 2003 is recommended)
Microsoft Internet Explorer 4.01 SP1 or later
Hard-disk drive with 12 to 65 MB of available hard-disk space (actual requirements will vary based on selection of features and user's current system configuration)
Available 9- or 25-pin communications port (adaptor required for 25-pin communications port), infrared port, or USB port (available for Windows 98, Windows Me, Windows 2000, and Windows XP only)
VGA graphics card or compatible video graphics adapter at 256 color or later
Keyboard
Microsoft Mouse or compatible input device
Options for Windows XP, Windows 2000, Windows Millennium Edition, Windows NT Workstation 4.0, or Windows 98
Audio card/speakers for sound
Microsoft Office 97, Office 2000, Office XP, or Office 2003
Modem for remote synchronization
Ethernet local area network connection for remote synchronization
"
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