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By default, there is no way to do so. i also google it and can't think of a way to do this easily. <br />
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customized this could take a long shot. <br />
What is the business case of this?
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Thank you. The idea that some people been delegate by their company to handle two position in case that some in leave or quit temporary. I found that it's can be done by create two signature and select between them if needed.
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How to customize new email to show alert that give user list to select which signature he would add to the email before send or when he open it?
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How to customize new email to show alert that give user list to select which signature he would add to the email before send or when he open it?

Outlook Singature

Visual Basic for Applications (VBA) enables building user-defined functions (UDFs), automating processes and accessing Windows API and other low-level functionality through dynamic-link libraries (DLLs). VBA is closely related to Visual Basic and uses the Visual Basic Runtime Library, but it can normally only run code within a host application rather than as a standalone program. It can, however, be used to control one application from another via OLE Automation. VBA is built into most Microsoft Office applications.

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.