War story: the hardest bug I ever debugged

I had something like this once.

Vendor provided an outlook plugin (ew) that linked storage directly in outlook (double ew) and contained a built in pdf viewer (disgusting) for law firms to manage their cases.

One user, regardless of PC, user account or any other isolation factor, would reliably crash the program and outlook with it.

She could work for 40 minutes on another users logged in account on another PC and reproduce the issue.

Turns out it was a memory allocation issue. When you open a file saved in the addons storage, via the built in pdf viewer, it would allocate memory for it. However, when you close the pdf file, it would not deallocate that memory. After debugging her usage for some time, I noted that there was a memory deallocation, but it was performed at intervals.

If there were 20 or so pdf allocations and then she switched customer case file before a deallocation, regardless of available memory, the memory allocation system in the addon would shit the bed and crash.

This one user, an absolute powerhouse of a woman I must say, could type 300 wpm and would rapidly read -> close -> assign -> allocate -> write notes faster than anyone I have ever seen before. We legitimately got her to rate limit herself to 2 files per 10 minutes as an initial workaround while waiting for a patch from the vendor.

I had to write one hell of a bug report to the vendor before they would even look at it. Naturally they could not reproduce the error through their normal tests and tried closing the bug on me several times. The first update they rolled out upped it to something like 40 pdfs viewed every 15 minutes. But she still managed to touch the new ceiling on occasion (I imagine billing each of those customers 7 minutes a pop or whatever law firms do) and ultimately they had to rewrite the entire memory system.

> Vendor provided an outlook plugin (ew) that linked storage directly in outlook (double ew) and contained a built in pdf viewer (disgusting) for law firms to manage their cases.

I still don't understand how we've arrived at this state of affairs

Look I supported a few different legal platforms in that role and while I hated it, it was also the best.

Heres what a lawyer does:

1. They bill for time writing emails and on phone calls 2. They bill for time reviewing emails. 3. They bill for printing (and faxing if they are diehards) 4. They also bill for the time they are face to face with a human.

They also need to gather all the data, much of which flows in and out via email (or fax if they hate you) related to the case in a single space.

The sad state is that 80% of this can be achieved in outlook without much effort. Setting up an external application to capture all this shit is quite difficult, and generally requires mail to be run through it in some capacity. The question is, why reinvent the email client. (Sadly they reinvented the pdf reader) I have seen some lawfirms literally saving out every email as html, and uploading it with billing stats to a third party app. Its easier for me to support but the user experience can be awful.

The user already exists in Outlook, they already understand outlook. A few buttons in the ribbon (Mostly File this under X open case, time me, and bill this customer) make more sense from a user perspective.

From a support perspective its an absolute nightmare. Microsoft absolutely wont take a support case about an addon with shit memory management. And the addon provider will usually blame Microsoft.

This is close enough to the "can't log in to computer when standing up" bug... someone had swapped the keycaps for D/F (for example) so when 5-star general tried to log in when standing up he was typing "doobar" instead of "foobar" into the password field.

With the lady, if she'd dialed it back a bit on her pace of work "because people are watching", that could have been a crazy one to debug... "only happens when no one is watching (and I'm not beastly-WPM closing cases)"

Love it! I hope you got her a plaque or something. It’s like John Henry vs. the steam engine.