6 Everyday Tasks Technology Has Made Needlessly Hard for Wisconsinites

Paying a Milwaukee property tax bill online costs an extra 2.75%, with a $3 minimum. Madison charges 2.45%.

Paper checks are still free.

Wisconsin has moved a stack of everyday errands online, and a few of them got harder in the move, not easier.

These are the everyday tasks technology has made needlessly hard for Wisconsinites.

Note: This is general information, not legal advice. Renewal rules, fees, deadlines and online systems for licenses, benefits, permits and payments are subject to change.

1. Scheduling a Social Security Visit

Wisconsin’s Social Security field offices are spread across 26 locations in 24 cities, from Superior on Lake Superior to Kenosha on the Illinois line.

That distance used to matter less, since a Wisconsinite could walk into whichever office sat closest and simply wait a turn.

Not anymore.

As of January 2025, the Social Security Administration requires an appointment before a Wisconsinite can see a representative in person, booked online or by calling 1-800-772-1213.

A caller from Superior competes for that same national line as a caller from Kenosha.

Wisconsin’s spread-out map of field offices does nothing to shorten that wait once the phone system takes over from the front desk.

2. Renewing a License or ID

Wisconsin’s Division of Motor Vehicles (DMV) lets many drivers renew online, and that part saves a trip.

The trouble starts with what the online system can’t do.

A legal name change or a first-time upgrade under the REAL ID Act (REAL ID for short) sends Wisconsinites back to a DMV counter in person.

So does a driver’s license that’s been expired for more than a year.

Even a driver who qualifies for the online path doesn’t fully skip the counter.

The Wisconsin DMV prints only the photo already on file onto the new card, and a phone or webcam selfie only confirms identity during the transaction.

Anyone who wants a current photo updated still has to show up at a DMV Customer Service Center.

A renewed license keeps the same number as the license it replaces.

Only the photo must match.

3. Buying a Hunting or Fishing License

Wisconsin’s Department of Natural Resources (DNR) sells hunting and fishing licenses through an online system called Go Wild.

Setting up a Go Wild account on your own requires a valid driver’s license number.

The system uses that number to confirm your identity and let you use the license itself as proof of purchase out in the field.

Many Wisconsinites don’t have a driver’s license.

A resident 18 or older who has given up driving, or who has only ever carried a state ID, can’t finish that account setup on the website alone.

The DNR’s instructions send that person to a call center to get the account built by phone instead.

A fishing license used to cost a stop at the hardware store counter.

Now it costs hold time.

4. Paying Your Property Tax Bill

Wisconsin cities and counties that accept property tax payments online almost all attach the same catch: A credit or debit card comes with an extra fee.

Milwaukee, the state’s largest city, charges a 2.75% fee with a $3 minimum, and Madison charges 2.45% through its online system.

A transfer straight from a checking or savings account, called an Automated Clearing House (ACH) payment, skips that fee in Milwaukee and many other Wisconsin systems.

Setting it up still means creating an online account first.

Skipping the online system altogether means mailing a check or dropping it in a drop box instead, and neither option takes cash.

The mail and drop-box options are the only way around the card fee these Wisconsin systems charge.

Paper still beats the surcharge.

5. Filing an Unemployment Claim

Wisconsin’s Department of Workforce Development (DWD) built its unemployment insurance system to run online first.

A claimant only reaches a phone line for the situations the online system can’t handle.

That phone line keeps limited hours across the week, closed weekends and running a shorter day on Thursdays.

Monday and Tuesday bring the longest waits on that line.

A claimant stuck on a technical problem the website won’t solve waits in that same line as everyone else.

Timing the call still matters.

6. Paying to Ride the Rapid Bus

Madison and Milwaukee, Wisconsin’s two biggest cities, both run Bus Rapid Transit lines that work more like light rail than a regular city bus.

Milwaukee County Transit System (MCTS) opened its CONNECT line in June 2023, and Madison’s followed in September 2024.

Handing the driver a couple of dollars stopped working on those routes.

In Madison, cash isn’t accepted once a rider boards at a Bus Rapid Transit station.

A rider without a pass or an app has to buy a ticket at the ticket machine on most platforms first.

Milwaukee’s CONNECT line works the same way in spirit.

Riders there must prepay and validate a fare at the station before boarding, whether they’re paying with the Umo app, a WisGo card, a credit card, or cash.

Miss the machine, and the bus leaves without a paid fare.

No machine means no ride.

The One Discount That Still Runs on Paper

Milwaukee County Transit System runs a reduced-fare program that technology has never touched, and that gap makes it the hardest task on this list.

The WisGo Reduced Fare Card cuts fares for Wisconsin riders age 6 to 11, seniors, riders with disabilities, and Medicare enrollees.

Getting the card isn’t a quick online form.

A rider has to download and print a paper application.

Anyone applying under the disability category needs a treating physician or another licensed health care provider to sign the back of it.

The finished application, a copy of a photo ID, and a recent photo then have to be mailed to MCTS or dropped off in person.

Riders who skip all that can still board with exact cash at the reduced rate.