As I’ve previously noted, I use a lot of parentheses in my writing. It’s not uncommon for me to be hastily composing a post and realize that I’m about to end a parenthetical thought as well as its mother sentence. Assuming that the parenthetical thought is a grammatically complete sentence, how should one punctuate?

I default to punctuating both inside and outside the parenthesis (this tends to look pretty tacky.). Jane Straus from grammarbook.com seems to think this is correct. I’ll note that ending a parenthetical thought in an abbreviation looks pretty bad as well, but is almost certainly correct (something ending in a list including this, that, etc.).

Continuing with this predicament, what are we to do with parenthetical exclamation or interrogation (this looks ridiculous!)?

The Chicago Manual of Style offers some guidance here, bolded for emphasis.

For some reason, questions about periods have dominated the Q&A mail lately. Why the sudden confusion? Why, after a lifetime (I trust) of never encountering two periods in a row, do readers suddenly think this might be a good idea? In any case, here are some answers: Don’t ever put two periods in a row. Put one period at the end of a declarative sentence, even if it ends with an abbreviation or a URL. (Questions and exclamations use question marks and exclamation points instead of a period, not in addition to one, even in quotations.) A sentence that stands alone within parentheses needs a period inside the parentheses with it. (Here’s an example.) A sentence in parentheses within another sentence does not take a period, because the period is reserved for the main sentence (questions and exclamations, however, must have their respective marks!). An abbreviation that ends with a period must not be left hanging without it (in parentheses, e.g.), and a sentence containing a parenthesis must itself have terminal punctuation (are we almost done?). Finally, an abbreviation ending with a period that is immediately followed by a question mark or exclamation point requires both marks (Q.E.D.!).

I think I’m actually way more confused after reading that. A few other guidelines that come up in Google recommend never using the .). for parenthetical sentences-in-sentences, that the external period is sufficient in these cases.

Next up, what about quotes? Between n8henrie.com and the SMRT Blog, I write a lot of how-to posts, and in many of these I use quoted phrases to set apart an exact string of characters or words. Usernames, URLs, and Google queries are common examples.

In American English, punctuation at the end of a sentence comes inside of a closing quote. Is it considered incorrect to place this punctuation outside of the quote if the quote is being used to set apart an exact phrase? For example,

Set the server to “http://www.example.com”.

I wouldn’t want to put that period inside the quote and confuse people trying to follow my instructions, so I think it is reasonable in these cases to place the punctuation outside of the quotes. However, I’d rather know if it were correct in addition to reasonable, since I am occasionally writing these instructions in reports destined for VIPs in the school of medicine.

In this case, grammarbook again suggests that what I’ve been doing is okay, at least for question marks, semicolons, and a few others. The APA style guide offers similar advice, although neither specifically address the case of trying to communicate an exact phrase that also happens to be at the end of a sentence requiring a period.

The most common answers that I’m seeing on forums (fora?) is to simply rewrite or rearrange the sentence to avoid the problem entirely. I don’t like that answer, but it’s probably easier than… writing this post.

Any fellow tech bloggers want to chime in with your approach?