Now, AFAIK - there's no real way to resize a caption box, once it's added to screenshot (as an object).
Problem: Unless user's have developed high level of estimating how many characters and / or lines, at given font type & size, will fit in what seems like a set height for caption box, it's hard to know that the text entered will fit, once caption is added.
There is the option to use \n (buried deep in Help file), at the end of text lines, as they're entered in caption box, but it's not very convenient & you have to remember whether to leave spaces before / after entering \n, or you'll still have to edit spacing, once caption is added. You also have to estimate where each " \n " should be entered, while creating caption, so lines don't run past width of caption box (usually same as screenshot width). That's critical since caption box size isn't currently re sizable.
If resizing caption objects after they're added isn't possible / practical, then adding word wrap so text automatically fits the CURRENT screenshot length & automatic height adjustment of caption box, would eliminate guessing, speed up process of creating multi line captions & result in a more professional look.
Other screen capture editors use word wrap in caption boxes & automatically increase caption box height accordingly. Even the very old FastStone Capture 5.3 (last free version) used word wrap / automatic caption box height adjustment, when entering text.
Other screen capture editors allow adding additional caption boxes ("stacking" - w/ or w/o borders), if desired - such as FastStone Capture & others.
For users only needing VERY short, one line captions, it's fine as is. For more technical uses, the caption often requires more in depth explanation of the screen. On some screens, you don't want to cover the shot w/ extra text boxes. Also, for more professional presentations, having a better formatted caption box, including word wrap & auto height adjustment of the box, would allow not adding text boxes over the screenshot, when that's not desirable.
FastStone Capture Caption Boxes
Even though the jpg size of the FastStone image is smaller than SSC image (no special settings were used in FastStone, for HQ), the shot looks better than SSC. Perhaps that's due to some setting in SSC.
Screenshot Captor Caption Boxes
I don't see an option (not easily found) to change width of border around SSC caption box. Would be easier / faster if controls for caption box properties were on caption box UI (options button).
It's unintuitive as to which properties from which right menu item controls EACH separate caption box property.