How much do you know about playing the stock market with options?

The following are highlighted options insights and ideas from

TheStreet.com

.

From

Options Expiration: Three Things You Need to Know

:

1. Beware Overnight Shorts in Index Options

Market tenterhooks -- and a 24-hour global news cycle -- mean traders should be mindful of overnight short-covering in index options. Kevin Fischer, head of the block trading desk at Interactive Brokers, cautions that option traders should be vigilant of index options with a.m. settlement -- index options, for which trading stops at 4 p.m. on Thursday night, but for which the cash settlement price is calculated on the following Friday morning, and based on the opening tick of the entire index basket.

For a cautionary tale, consider what happened upon last month's expiration, between the close of trading in the September option contract at 4 p.m. on Sept. 18 and the calculation of the settlement price on the morning of Sept. 19.

Read the full version of

Options Expiration: Three Things You Need to Know

.

Jud Pyle (Mad About Options, ONN.tv):

All right, so the

CBOE Volatility Index

(VIX) is climbing higher again -- last check

midday Oct. 15, the "fear barometer" was up 18% and had pushed atop the 65 level.

Given the market's precipitous drop today, this isn't all that surprising. What

does

give me pause is that an options trader out there is bidding 10 cents per contract for 1,000 of the VIX October 100

calls

. (No one has sold these contracts yet). These calls expire Wednesday, October 22, or 30 days before the following month's

S&P 500 Index

options expire. What's more, these calls would only become profitable if the VIX rallies another 50% by next week.

Mad About Options: Guarded on Google (Video, Oct. 15)

Jud Pyle and Matt Buckley review Jim Cramer's recent bearish comments about

Google

(GOOG) - Get Report

and offer an appropriate options strategy. Pyle and Buckley also offer options ideas for

Precision Cast Parts

(PCP)

and

Microsoft

(MSFT) - Get Report

.

To watch the video, click the player below:

var config = new Array(); config<BRACKET>"videoId"</BRACKET> = 1856957815; config<BRACKET>"playerTag"</BRACKET> = "TSCM Embedded Video Player"; config<BRACKET>"autoStart"</BRACKET> = false; config<BRACKET>"preloadBackColor"</BRACKET> = "#FFFFFF"; config<BRACKET>"useOverlayMenu"</BRACKET> = "false"; config<BRACKET>"width"</BRACKET> = 265; config<BRACKET>"height"</BRACKET> = 255; config<BRACKET>"playerId"</BRACKET> = 1243645856; createExperience(config, 8);

Plus, don't miss these other recent Mad About Options videos on

TheStreet.com

:

Talking QCOM

(Oct. 14),

Hooray for J&J

(Oct. 14) and

Emerson's Faulty Plug

(Oct. 13).

For more information about Mad About Options, visit

www.ONN.tv

.

Image placeholder title

From

Dykstra: Grinding Out the Wins

Monday

Oct. 13 I

Lenny Dykstra picked up a quick $1,000 win with

Microsoft

(MSFT) - Get Report

, a company I have already won with earlier this year. I recommended buying 10 contracts of the January 2010 $17.50 calls (WMFAX) on Oct. 8 and the order was filled two days later. In just three days, I picked up an easy $1,000 on an investment of $7,700.

Read the full version of

Dykstra: Grinding Out the Wins

.

Editor's note: Lenny Dykstra will explain his deep-in-the-money call options (now 73-0 for the year) at TheStreet.com Investment Conference on Saturday, Oct. 25. Limited seating. Act now.

From

Use Bear Spreads When the VIX Is Sky-High

:

Late in the day

Oct. 10, it got even crazier, as the

Dow

would pull back toward the lows and then rally almost 900 points up to higher highs and then sell off more than 400 points in the final minutes back into negative territory. That was another 1,300 points in the last 75 minutes.

That's a lot. That's one reason we saw the VIX explode to all-time highs of 76.94 late Friday

Oct. 10. The other reason is the continued desperation on the part of option traders to buy

puts

.

VIX
New highs and the ultimate buy signal

Click here for larger image.

Source: optionsXpress

This brings me to the issue of the day: how to buy protection in this environment where puts are astronomically high.

There is a way, and it is a fairly simple procedure. You cannot just go out and buy put premium at will (especially when the market is collapsing), because you can create serious losses paying up for all that bloated premium when you buy puts into weakness. But you can leg into bear spreads all day long. You wait for a pop (like the kind we had Friday morning after the early low) and use the pop to buy the at-the-money puts like the

PowerShares QQQ Trust

(QQQQ)

October 32 puts. Then wait for the selloff to write the October 30s or 31s. Doing this over and over creates bearish positions (put spreads) with limited cost and minimal risk to the upside.

Read the full version of

Use Bear Spreads When the VIX Is Sky-High

(

RealMoney

access required).

For more on options, bookmark and visit TheStreet.com's

Options/Futures page

.

This article was written by a staff member of TheStreet.com.