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I currently have a bug in my Mac's Terminal (I actually use iTerm2 but it's still there), where once I press left arrow after typing, I can't go past the last character.

Is there a way I can modify my .inputrc to insert an extra space, whenever I press the left arrow key when my cursor is at the end of the line?

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    Have you looked at this post? – demure Jun 1 '13 at 0:55
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Not exactly sure what you are asking.

It is perfectly normal that, in vim, if you go to the end of a line in insertion mode it position the cursor is on what looks like an empty space at the 'right' of the line, but in command mode (ie after you press escape) this empty space disapears (and the cursor goes back to the previous character).

This is because in insertion mode, vim puts the cursor on the position on which the next character you type will be inserted. So this space does not exist in your document, and this has nothing to do with your terminal.

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