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I know I can hold down shift to drag a line constrained to 45° or 90° with the pen tool in illustrator. However, I'd like to see the line previewed interactively as I draw. I can get that behavior with the line segment tool, but need multiple segments linked together. Is there a way to do this?

(Obviously one option is to draw all of my segments individually with the line segment tool and then join them together, but then I have to do a lot of post-hoc adjustment to the joins if I didn't line up the ends perfectly in the first place.)

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I don't think this is possible. What you're seeking is a sort of "rubber band" preview similar to Photoshop. Illustrator simply doesn't have that or anything similar.

There are third party plug in which do this, but this alone wouldn't be enough reason to purchase third party items. At least not in my opinion. Astutegraphics.com has InkScribe which is part of the VectorScribe plug in. InkScribe contains a Rubber Band option:

inkscribe panel
inkScribe

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    you can click and hold the mouse and hold the space bar down to get you a rubberband with a movable anchor, but you cannot combine that with the angle constraint hot key (shift space changes to the hand tool) AFAIK.
    – horatio
    Commented Apr 25, 2013 at 17:11
  • Good point about the space bar.
    – Scott
    Commented Apr 25, 2013 at 17:23

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