Outgoing - If I send an email from Outlook to my test contact, should the email appear in CRM against my test contact?
No
Incoming - If I send an email from gmail from my test contact, should the email appear in CRM against my test contact?
No
Replying Outgoing - If I reply to an email in Outlook, should the email appear in CRM against my test contact?
Yes(if reply is to the email originating from CRM)
Replying Incoming - If I reply to an email in gmail, should the email appear in CRM against my test contact?
Yes(if reply is to the email originating from CRM)
However, these are configurable.
"When you use Microsoft Dynamics CRM for Outlook, all the e-mail you receive arrives in your Outlook Inbox. Only e-mail messages that originated as a Microsoft Dynamics CRM e-mail activity (that is, a response to e-mail message you send from Microsoft Dynamics CRM) or that is marked as tracked in Microsoft Dynamics CRM, arrives in the Microsoft Dynamics CRM Activities and My Work: Queues area. If you prefer, you can:
Track all incoming e-mail messages as Microsoft Dynamics CRM e-mail activities.
Track only e-mail messages that originated in Microsoft Dynamics CRM (that is, e-mail sent in response to a Microsoft Dynamics CRM e-mail activity) into Microsoft Dynamics CRM e-mail activities.
Track only e-mail messages related to your accounts, contacts, or leads.
Track e-mail messages related to all Microsoft Dynamics CRM and custom record types that contain an e-mail field."
Please read :
download.microsoft.com/.../Microsoft_Dynamics_CRM_2011_User&;s_Guide.doc
You can go to "Managing E-mail Activities" section, it details out everything you need to know.
Thanks,
PS