I'm sure many of us used to work for tips, or perhaps still have side jobs that involve tips (I certainly did when I started reading FT).

Don't most restaurants now just process CC tips all together and then dump them into the employees' paychecks (either specific to a person or out of a split pool)? It's not like servers are raiding the cash register at the end of each shift and having to count out pennies.

My former job was as a valet/doorman, so all of my tips (and the majority of my pay) was in cash, which we did have to physically split up at the end of each shift. We'd actually do a split/cash out every time someone arrived or left, since partial shifts weren't out of the ordinary. Naturally, most of our tips were in whole dollars. But there would always be a few guests every shift who would hand us some quarters or whatever pile of change they had in their car/pocket/bag/whatever.

In three years working there, I can't remember a single time anyone even thought about turning down a tip or complaining because it wasn't a round number (there was of course plenty of valid complaining about people who did not tip appropriately for whatever service they asked for). If we ended up with just a few coins, someone would grab candy or something from a vending machine during a break or something that we'd all share. If we had a lot of coins, we'd get the front desk to swap out for paper money before we did a split. Maybe a couple guys would take some coins to go play quarters out back after they got off work. It just wasn't a big deal.

Not at all
 

Waitressed during college and a few years after (great money, good times).
Never minded rounding up, change is always needed when shopping or out and about. And for the change jar.
However, the restaurant did not like to have change on hand in the cash register to accommodate every server's tips change.
Advice: do what's best for for you.

I almost always round to the nearest dollar, usually up. I have never, ever had a server complain or even give me the stink eye for leaving, say, a $6.72 tip instead of $7, or as many people would have, $6.

I suppose for those servers who take their tips as cash at the end of the shift, it's a bit more a hassle to count out the change, but if that's your biggest problem in life, you're doing fine.

I always adjust the tip to make the last 3 digits the same. Its a way to check no manipulation afterwards and also a nice mental challenge.

My last 3 meal payments were 78.88 114.44 32.22 with tips included of 7.88 10.64 and 3.22

That happened to me once. I saw a restaurant on my CC bill (I'll mention that it was in Door County since you're from MKE ;) ). It wasn't even and seemed high. Got all mad, told the wife. Checked the menu. Nope, place was just overpriced. Then I remembered that the service had been poor, I'd left a smaller tip, but had tipped and rounded. Server hadn't put in the tip at all.

Sometimes, I just put the rounded amount on the merchant copy of the charge and don't fill in the tip amount. Why risk a math error after a couple of adult beverages?

I see this done all the time when done on a cc. For cash though, perhaps rounding at least to the nearest quarter is good enough, but I often make it to the nearest whole unit closest to the 18% range.

And don't forget in Europe where places like the Euro is currency, it's common to round up to the nearest dollar as a tip (if one were to tip since it's not the norm).

Yes, but do you work for one of them?

We're on per diems for meals when on travel, so it's a moot point, but for other business meals, the company policy is that the tip should be "reasonable." They don't specifically say must be 20% or less, and indeed, I have never had a problem getting reimbursed for going a bit over 20% (like I said, I usually round up to the nearest dollar within 20%, usually post-tax unless the meal was very short and the bill very high).

Stimmt So!
 

Keep the change. I know people who do the same thing because they like rounded amounts.