Question: You recently mentioned 301 redirecting one of your sites. How do you tell if 301 redirects count?
Answer: This is very similar to testing if a link pointing at your website is passing link juice. Before 301 redirecting your site, find at least one navigational type search query that can be created out of the inbound anchor text of the site you are redirecting, which you would still expect to rank for even if you had no page content.
When the new site ranks well for that query you know the search engine is following your 301 redirect, though it might take a bit longer for the trust to propagate through the new website and get your contents fully indexed. As time passes you will see the new site replace the old site for more and more search queries. If it ever stops ranking you know there is a technical error with the redirect (such as accidentally writing over your .htaccess file) or they are no longer trusting or following the redirect.
If you are a large corporation or large Google advertiser then Google will go out of their way to work with you to ensure the redirect counts and the transfer is smooth. Here is an example post Matt Cutts made about helping migrate Microsoft Live Spaces:
By the way, it looks like the primary issue with the Windows Live Writer blog was the large-scale migration from spaces.msn.com to spaces.live.com about a month ago. We saw so many urls suddenly showing up on spaces.live.com that it triggered a flag in our system which requires more trust in individual urls in order for them to rank (this is despite the crawl guys trying to increase our hostload thresholds and taking similar measures to make the migration go smoothly for Spaces). We cleared that flag, and things look much better now.
If you are an SEO working on a smaller mom and pop type website and rank better than search engines feel you deserve to they may manually penalize your site. Some search engineers might decide to kill the redirect because they generally think of SEOs as being manipulative scum (even if they are unwilling to admit that publicly).
Having seen friends move many sites, the only 301 redirect penalties I have come across have been manual ones. From my experimentation Google is not very good at algorithmically detecting search relevancy manipulation based on 301 redirects, but they may flag and review some of the higher authority cross site 301 redirects.
If the site you are redirecting has anything shady going on with it, or if you are a well known SEO, make sure you do not discuss the redirect publicly or register your sites with Google Webmaster Central, otherwise Google might kill the redirect out of their distaste and hatred for the field of SEO. A better way to use the old trusted site might be just to try to make it look legitimate and use it as a link source for your more profitable websites.
If you are a smaller webmaster and still want to risk redirecting your site you want to have press pages, an about us page, and give lots of other signals that you are larger than you are, in order to help minimize the chances that a Google engineer will try to destroy your rankings.
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