If I know a company is going out of business, can I lose by Short-Selling?

You likely couldn’t find anyone writing put options on stocks that aren’t widely traded.

Say wha?

http://www.dechert.com/library/FS_34_10-08_Regulation_SHO.pdf (pdf)

Rules for market makers are different that rules for everyone else. They are provided limited exemptions from the locate requirement.

True, many stocks don’t have an activity quoted market. If you really wanted to, you would probably have to speak directly with someone on the floor of the Chicago Board Options Exchange and ask for them to make you a market.

I see that now, and it looks like it’s not just limited to options MMs, but all MMs?

It appears they get 6 trading days (see page 37) to close out the naked short before they have to buy shares on the open market to return to the original borrower.

Right now the old GM is still selling, for under a dollar a share, despite warnings that it is foolish.
Everyone involved tries to tell buyers that it’s not the new GM, and that soon the shares will disappear, but apparently it’s still legal to sell if you find a confused buyer.

There are exemptions for market makers in stocks, as well. I make my living as a trader at a trading firm. It’s not uncommon to see what appears to be naked short selling by market makers.

An example:

Illiquid stock XYZ has an average daily volume of 2000 shares. It’s priced at $5. Overnight, some huge positive news comes out. At the open there is an overwhelming imbalance of buy orders. Because the stock is extremely thinly traded the buy orders spike the stock violently up to $10 - there is no stock offered. I see this happening and ask our stock loan desk to see if they can locate shares for me to sell short into the buy orders. They check their inventory and call around to other institutions. They can’t find anyone that has any to lend, and I’m out of luck. Sooner or later Knight, Citadel, or Hudson, etc. will show up offering large amounts of stock. This means that they either had large amounts of stock in their own inventory, they were able to locate and borrow a large block, or they are naked shorting.

That is the kind of situation for which the exemption exists.

A variation on the question:
Suppose I get some put futures (lets say $10/share) and the corporation goes kablooie like Enron and the banks. Do you make $10 x # of shares?

I was going to mention GM but Dances with Dice beat me to it. GM stock stayed above 1 for the longest time even though everyone KNEW it was going to become worthless. It dipped to ~.70 after the bankruptcy announcement then rocketed to ~$1.20 the day after. If you had tried to short sell that stock you would have probably lost all your money. Be careful betting against the stupidity of idiots. I had heard there was a 50% charge to borrow the shares but I could never locate any to borrow (I was curious) so I don’t know personally.