An old question, but hoping it will be useful to others.
You can set that artifacts will be automatically updated when a project is created, instead of manually creating artifacts with each update: open the project settings ( File -> Project Structure ) and on the Artifacts tab check Include in project build (screenshot of IntelliJ IDEA Ultimate 2017.1 ):

Edit:
To ensure that artifacts created automatically when the source changes are similar to automatic assembly, see the procedure described in @CrazyCoder's answer, which was commented above:
deploy / debug Java code on a remote server using Intellij
Indication of additional necessary steps from this answer adapted for IntelliJ IDEA Ultimate 2017.1:
- Open
File -> Settings -> Build, Execution, Deployment . - In
Options set Upload changes files automatically to the default server to On explicit save action (Ctrl + S) . - Check the
Upload external changes box below.
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