Forum Moderators: Robert Charlton & goodroi
At PubCon Matt Cutts said that googlebot will follow a chain of up to ten redirects. In practice, I'd say that's a pretty dangerous thing to try. For one thing, it seems to me that only a percentage of the link juice actually passes through any one redirect (maybe 85% or so). If you have a long chain, then you start compounding that loss of link juice.
And another negative is that Google needs to check any redirect for trust - it's not some instantaneously applied factor in the algo. Throw them a long chain of redirects and you are potentially extending the time it takes to have the link juice applied.
If you have internal links pointing to a url which you then further redirect, this can look suspicious. Too much of that kind of thing might result in the end of the chain getting dropped from the index, at least for a while.
As many have said, the best thing to do is not to chain redirects at all. Use the 301 springly and when you do, work to make it occur one hop.
