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Chief, I guess you type faster than I do! 
You have to use a special pump with built in gauge that screws in the shock's fill valve before touching the valve core allowing any air to escape, then keep on tightening it and then you will hear the woosh from the connection with the air in the chamber. The gauge will then show you how much pressure you have in. It is recommended to do so with the bike's rear lifted up so the tire is not touching the ground, and the shocks are in full extended position. Once your air pressure is showing on the gauge, pump air in the shocks.
Kaw makes a pump, HD does also; many have used a bicycle tire pump, I have even heard that an air compressor with the regulator turned way down will work, but I have never been brave enough to try that one. About 43 PSI max, seal damage will occur if too much pressure is added.
Don't use tire air gages to check and don't use compressed air to air up. You really need a lossless pump with a gage to both check and adjust air in the shock. Progressive Suspension makes a very good pump with gage.
http://www.vulcandrifterriders.com/blog/?p=590
The shocks should be at room (ambient) temperature and the rear wheel/suspension raised off the ground.
Adjustment info can be found in the mods/tips area... Kaw suggest 43psi for the HARD setting, Heavy loading, and/or Bad road. You can adjust anywhere in between. The pressure should never exceed 71psi or you will blow seals. When using the pump you will occasionally see some oil in the pump tube, that's not a problem.
what is the proper way to air up the rear shocks on a 1999 1500 ?
if the bike came with a specific pump...i don't have it.
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