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I just checked our server logs to see how many times Googlebot had visited over the past hour, and see that it was about 100 pages visited during this time (This was just a totally random check). Also about 25 visits from Yahoo Slurp.
So now, I'm really concerned about the 15 - 20 minutes of downtime. I guess I just have to hope that Googlebot doesn't visit during the downtime, but what if it does? If it visits our main page, and gets a 404 error, will it ever bother to come back? We are in the top ten for Google for our main search terms, so this worries me a lot right now.
Does anyone have any experience in this, and is there anything that I can do to avoid a problem with Google not being able to find pages for a short period?
If for some reason you have to reload the whole site after the upgrade, then you might want to figure out how to turn the site off temporarily, either through whatever control panel is available to you or via a .htaccess file (I think that can be done but I'm not 100% sure).
So now, I'm really concerned about the 15 - 20 minutes of downtime.
I wouldn't worry too much. It's not going to dump you because it can't find you once or twice. If the site were down for a week or two it might be more serious. Most of the SE's seem to be pretty good about accepting short periods of down-time, (if they weren't, there'd be a lot less sites indexed).