I am debugging a (native) multi-threaded C++ application under Visual Studio 2008. On seemingly random occasions, I get a "Windows has triggered a break point..." error with a note that this might be due to a corruption in the heap. These errors won't always crash the application right away, although it is likely to crash short after.
The big problem with these errors is that they pop up only after the corruption has actually taken place, which makes them very hard to track and debug, especially on a multi-threaded application.
What sort of things can cause these errors?
How do I debug them?
Tips, tools, methods, enlightments... are welcome.
Application Verifier combined with Debugging Tools for Windows is an amazing setup. You can get both as a part of the Windows Driver Kit or the lighter Windows SDK. (Found out about Application Verifier when researching an earlier question about a heap corruption issue.) I've used BoundsChecker and Insure++ (mentioned in other answers) in the past too, although I was surprised how much functionality was in Application Verifier.
Electric Fence (aka "efence"), dmalloc, valgrind, and so forth are all worth mentioning, but most of these are much easier to get running under *nix than Windows. Valgrind is ridiculously flexible: I've debugged large server software with many heap issues using it.
When all else fails, you can provide your own global operator new/delete and malloc/calloc/realloc overloads -- how to do so will vary a bit depending on compiler and platform -- and this will be a bit of an investment -- but it may pay off over the long run. The desirable feature list should look familiar from dmalloc and electricfence, and the surprisingly excellent book Writing Solid Code:
Note that in our local homebrew system (for an embedded target) we keep the tracking separate from most of the other stuff, because the run-time overhead is much higher.
If you're interested in more reasons to overload these allocation functions/operators, take a look at my answer to "Any reason to overload global operator new and delete?"; shameless self-promotion aside, it lists other techniques that are helpful in tracking heap corruption errors, as well as other applicable tools.
Because I keep finding my own answer here when searching for alloc/free/fence values MS uses, here's another answer that covers Microsoft dbgheap fill values.
You can detect a lot of heap corruption problems by enabling Page Heap for your application . To do this you need to use gflags.exe that comes as a part of Debugging Tools For Windows
Run Gflags.exe and in the Image file options for your executable, check "Enable Page Heap" option.
Now restart your exe and attach to a debugger. With Page Heap enabled, the application will break into debugger whenever any heap corruption occurs.