I just tried your first playbook on 1.4.4 and it added both keys to the 
authorized_keys file. Are you sure that those keys are different files? 
Maybe you made a mistake an copied one key to another?

On Saturday, February 22, 2014 5:34:43 PM UTC+1, Yaniv Ferszt wrote:
>
> I'm using 1.4.4 and it is not doing that, it is only appending new keys to 
>> the current ones. Maybe something was changed in 1.5. Could you try 1.4.5?
>>
>
> same behaviour with version 1.4.5
>
> [yaniv@yfhv1 playbooks]$ ansible-playbook --version
> ansible-playbook 1.4.5
>
> here are the playbooks i have tested
>
> 1. 
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> *[yaniv@yfhv1 playbooks]$ cat ssh-keys.yml---- name: "Set up 
> authorized_keys for the root user"  hosts: laptop  user: root  tasks:  - 
> name: Set up authorized_keys for the root user    authorized_key: user=root 
> key="{{ item }}"    with_file:      - 
> /home/yaniv/playbooks/public-keys/user-a      - 
> /home/yaniv/playbooks/public-keys/user-b*
>
> only the key from user-b stays in the authorized_keys file. even if i run 
> it multiple times.
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> 2.
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> *[yaniv@yfhv1 playbooks]$ cat ssh-test.yml---- name: "Set up 
> authorized_keys for the root user"  hosts: laptop  user: root  tasks:  - 
> name: Set up user-a authorized_keys for the root user    authorized_key: 
> user=root key="{{ lookup('file', 
> '/home/yaniv/playbooks/public-keys/user-a') }}" state=present  - name: Set 
> up user-b authorized_keys for the root user    authorized_key: user=root 
> key="{{ lookup('file', '/home/yaniv/playbooks/public-keys/user-b') }}" 
> state=present*
>
> same as before only the key from user-b stays in the authorized_keys file.
>
> 3.
> separated playbooks for every user same result. only the last executed 
> playbook is left in the authorized_keys file.
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> *[yaniv@yfhv1 playbooks]$ cat ssh1-test.yml---- name: "Set up 
> authorized_keys for the root user"  hosts: laptop  user: root  tasks:  - 
> name: Set up user-a authorized_keys for the root user    authorized_key: 
> user=root key="{{ lookup('file', 
> '/home/yaniv/playbooks/public-keys/user-a') }}" state=present*
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> *[yaniv@yfhv1 playbooks]$ cat ssh2-test.yml---- name: "Set up 
> authorized_keys for the root user"  hosts: laptop  user: root  tasks:  - 
> name: Set up user-b authorized_keys for the root user    authorized_key: 
> user=root key="{{ lookup('file', 
> '/home/yaniv/playbooks/public-keys/user-b') }}" state=present*
>
>
>

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