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Could anybody tell me if it is possible to have it automatically set so that when you enter text in a new box and it isn't able to fit, it expands the box rather than puts the words onto two lines? If that makes any sense...
Yes, one way to do it would be with Diagram Styles. Create a document with one box, put some text in it, open the inspector, choose the Resize to Fit option (last box in second row) and uncheck Wrap to Shape. Now do File->Export and choose OmniGraffle Diagram Style for the file type, and save the file in ~/Library/Application Support/OmniGraffle/Diagram Styles with a suitable name. Now whenever you want that treatment, you can choose Format->Choose Diagram Style... and select your diagram style.

Another way would be with the style tray at the bottom of the window. Make your first box as above. Now look at the style tray and look for the chit that handles Text:Autosizing (looks like a T in a box with little spacers around it). Drag that chit and drop it on the Shapes tool in the menu bar, and subsequent shapes you create will have that style. Or you can just drop it on individual objects. Yet another way would be with the style brush tool. In all of these cases, you create one box with the appropriate styling and then apply that to the others.

See the help relating to the style brush, style tray and diagram styles for more information.
Perfect. Thank you kindly.
Actually, having said that, when I follow the instructions and go to the OmniGraffle section in Application Support, it only shows me three folders, none of which are Diagram Styles. It shows me scripts, stencils, and templates. Could this be because I haven't purchased the full version yet. I'm on the trail version...
No problem, just create it with the New Folder button as you save the file. If you've created a Diagram Style in the past via another means, OmniGraffle will have already created the folder for you.

You can also create a Diagram Style that is a variation of an existing one by doing File->New Resource->New Diagram Style..., making your changes, and saving. OmniGraffle will create the folder for you if it doesn't exist.

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