I posted the same question on Stackoverflow, and got the answer I was 
looking for. Ugly, but it works.
http://stackoverflow.com/questions/42167747/how-to-loop-over-this-dictionary-in-ansible

On Friday, February 10, 2017 at 4:22:28 PM UTC-5, ZillaYT wrote:
>
> Say I have the following dictionary?
>
> war_files:
>   server1:
>   - file1.war
>   - file2.war
>   server2:
>   - file1.war
>   - file2.war
>   - file3.war 
>
>
> Now I want to iterate over this, say a get_url task:
>
> - name: Get the files depending on server name
>   get_url: src=http://some_host/{{ what to put here so I get each file 
> for the server }}
>   when: "{{item.key}} in ansible_hostname"
>   with_dict: "{{ war_files }}"
>
>
> IOW, if role is running in server1, it'll download file1.war and 
> file2.war; if running on server2, it downloads file1.war, fiel2.war, and 
> file3.war. I know there's probably other ways to do this, but I want to be 
> able to do iterate through all the dictionary values in a single task.
>

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