This is because Pamela is not allowed to access Skype due to a previous wrong answer to the access control question from Skype. Note below workflow is based on Skype for Windows version 3.2 and higher.

To check and fix this, follow these steps:

1. Open Skype and click on menu Tools, Options. Click on Advanced.

2. At the bottom of this page click on "Manage other programs' access to Skype".

3. A window will open that looks like the one below. It should show an entry called "PAMELA.EXE" but also may contain other programs. Click on Pamela and click the "Change" button.

4. You should see the window below. Select the top entry, this will allow Pamela to always communicate with Skype. Note that should you update your Pamela version, Skype will prompt again when you start Pamela asking you if the changed Pamela application is allowed to access. In that case, also select the top option.

After that Pamela should be able to connect to Skype and the icon should be pink instead of grey.

Should that not work, you will need to try deleting the Pamela.exe from the Skype list of external applications and let Pamela re-connect to Skype. The process is the same, however instead of "Change" you click "Remove" on the second screen shown in this article.