If you're using Jekyll, why not just host with S3/Cloudfront?

I had thought about it but

- I wanted to use Sinatra to 301 old tumblr urls

- Call me weird but I loathe seeing *.html in urls and that's the only thing you can do with S3 root object (when I checked a few months ago)

- something I can't remember. maybe it was cf edge server time to update when altering updates.

> I loathe seeing *.html in urls and that's the only thing you can do with S3 root object

You can configure name of index file, and that will be displayed for requests against root URL and subdirectories (such as blog posts) as well. No need for having .html in URLs.

The only problem I've encountered with S3 web hosting is that it does not let you host naked domains.

Naked domains as in "example.com" without the www? Just name your bucket without the www and it will work. You can then do a javascript redirect from a simple index page at www.example.com (google has said that they now follow javascript redirects. My play example "http://whitewatersearch.com

Where's the subtle flaw in this suggestion?

OK, here's a hint: we're talking about where to host besides Heroku because of Heroku's 76hr outage last Spring...

Last hint: Heroku itself is on top of AWS...

OK that was actually the answer.

I wonder how many hours would pass before you caught this and set up a new server? What if you're on vacation?

Honestly there's a little bit of "because I did it myself and I'm awesome it won't fail." That's hubris and very typical of young engineers.

Letting someone else manage it for you is probably the right thing for a startup to do. You just need to choose someone with a good, proven uptime record. That is what should guide your decision.. with so many things in engineering.