I'm assuming that the type of enrichedUser is supposed to be Maybe EnrichedUser and not Maybe [EnrichedUser], right?
If so, after extracting the [User] list from users :: Maybe [User], the problem you're facing is running a monadic action (to fetch the web page) for each User. There's a handy combinator for this in Control.Monad:
mapM :: (Monad m) => (a -> m b) -> ([a] -> m [b])
which can be specialized in your situation to:
mapM :: (User -> IO EnrichedUser) -> ([User] -> IO [EnrichedUser])
This says, if you know how to write a function that takes a User and creates an IO action that will create an EnrichedUser, you can use mapM to turn this into a function that takes a list [User] and creates an IO action to create a whole list [EnrichedUser].
In your application, I imagine the former function would look something like:
enrich :: User -> IO EnrichedUser
enrich u = do
let opts = ...
let url = "https://www.example.com/users/"
++ userToUserID u ++ "/addresses"
r2 <- getWith opts url
let Just enrichedUser = decode $ r2 ^. responseBody
return enrichedUser
where decode = ...
and then you can write (in your IO do-block):
r <- getWith opts "https://www.example.com/users"
let Just users = decode $ r ^. responseBody
enrichedUsers <- mapM enrich users
-- here, enrichedUsers :: [EnrichedUser]
...etc...
I've omitted the Maybe processing here for simplicity. If enriching fails, you probably want to somehow coerce a regular User into a default EnrichedUser anyway, so you'd modify the bottom of the enrich function to read:
let enrichedUser = case decode $ r2 ^. responseBody of
Nothing -> defaultEnrichment u
Just e -> e
return enrichedUser
and everything else would stay the same.