Hello,

I have a 1990 Westy  with very similar problem to the info I found below. For my van it usually takes anywhere from .5 miles to 1 mile to shift into 2nd gear. It is also usually after a few days of non-use. If I drive one day and then the next it will be fine about half the time. I recently changed the transmission fluid and changed the screen, and seems the same if not a little better than before. 

1. If it is a defective Automatic Transmission Governor (Where do you find these?)
2. If the governor is dirty/gunked up (How do you go about cleaning it?)

Any help on the above questions would be great. 

Regards,
Bill

Problem - "My '87 Westy automatic transmission operates well after about 2 miles, 
but will not shift into drive during the first mile or two of travel. 
This is only a problem on the initial trip per time period, ie. if the 
tranny is warm from recent travel it shifts fine."

Capt. Mike, Moderator, 10-25-2000 08:05 AM

Nice of VW to leave it out of the Vanagon edition of the Bentley, but 
the older Type II edition has an excellent troubleshooting chart for 
A/T's. Section 7-3.1.a.

Although your symptom could come from several causes, the prime suspect 
is #7: "Transmission stays in 1st gear with lever at 2 or D." Their 
probably cause is a. Governor dirty or defective; b. Valve body assembly
 dirty. There are a couple of others that may also be applicable.

I'm not too versed on A/T's but that you got an improvement with a 
screen cleaning and Dexron III change is encouraging. Tranny fluids do 
contain cleaning additives and if you have a blocked or sticky valve, 
it's possible it will work out as varnish dissolves or the piece of trash
 breaks free and moves to the filter. You might check with a reputable 
tranny shop to see if there's a safe and effective tranny cleaner 
additive. One that you can put in, run the specified miles, then drain 
and refill with fresh Dexron.

Do check your vacuum connections. A slight leak or deficiency, 
compounded by cold oil could leave you with incorrect vacuum until 
things warm up and seal.

Like oil changes in a gunked up engine, several changes in a short 
sequence could clear you out. Hope so rather than have to pull the 
tranny for a valve plate cleaning or worse.