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Despite being very similar to Rails, Middleman does not add a fingerprint hash to its asset paths by default. This means that when you write this:

<%= javascript_include_tag 'all.js' %>

... you always get the same path, regardless of the contents of all.js:

<script src='/javascripts/all.js'>

Because browsers tend to cache assets for a while, this means that users might not get your changes until their cache expires.

You can fix this by adding (or uncommenting) this in config.rb:

configure :build do
  activate :asset_hash
end

This will give your asset paths fingerprints:

<script src='/javascripts/all-3e02c23b.js'>

Note that the built files will now only include the fingerprinted version. There won't be an all.js anymore. So make sure to use helpers when refering to asset paths.