When operating a Tablet PC in slate / portrait mode, sometimes you have to think a little differently to do tasks that are second-nature with the keyboard.  One of those items is multi-selects. With a keyboard it is easy: click on the first item, then hold down the shift key and click on the last item. Or, hold down the Ctrl key, and select each individual item with your mouse.

What about the pen? Here are several tips to accomplish the same productivity shortcuts with a pen:

Shift Multi-Selects

Emails in Outlook

1. Move your pen to the left of the email icon
2. You'll see the pen cursor change from left-pointing cursor to a right-pointing cursor
3. Move your pen to the screen and then drag down to select the emails you want to move / delete

Building off of Craig's great Vista Tablet PC post, another option is to modify one of the Pen Flick edit gestures to toggle the Shift key, thus using a gesture to activate the Shift key.

You can also assign the shift key to an onscreen press / hold button in the Tablet PC settings.

Ctrl Multi-Selects

For Ctrl individual multi-selects ( selecting multiple individual items in a list ) I've assigned a press and hold button to the Ctrl key. You can do this in the Tablet PC settings found in the Control Panel. You'll want to use the Press and Hold option because you have to hold down the Ctrl key while selecting each of the items with your pen, which mimics what you do with the keyboard.

I experimented with a Ctrl gesture for individual multi-selects, but it doesn't work right since there is no way to mimic holding down the Ctrl key with a gesture. Once the gesture is activated, the key stroke activates then deactivates. The press / hold onscreen button is the best solution I've found for Ctrl individual multi-selects.