Dymo Printer

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A Dymo Printer can be used with a Windows/Mac computer and must be plugged in using a USB cord. If you would like to print to a Dymo printer from an Android/iOS station, use the Print to Another Station feature.

Printers and Labels

  • Printers: LabelWriter 550, LabelWriter 450 Turbo, LabelWriter 450 Twin Turbo, or LabelWriter Wireless, which has to be USB-connected at this time.


    The Wireless Printer is only available as a USB-connected printer for Desktop at this time. To learn how to set it up, follow the steps in the Dymo Wireless User Guide.


    For Dymo 4XL/5XL models to work, on each station, you will need to rename the printer driver to "Zebra Dymo" and choose the option to Rotate the label 90˚, found on the Printer Check page.

  • Labels: We designed our templates to work with the Dymo 30256 Large Shipping Labels. If you want to use the non-default sizes, you'll need to create custom labels.


    If using a Dymo LabelWriter 550, you must use Dymo brand labels and those labels must have the RFID sticker in the core.

  • Cleaning Cards: If you're experiencing any issues with the printer such as blank labels printing or dirty labels, you'll want to clean the printer. The printer might come with a few of those, but you can buy some more at Amazon.

Printer Setup

You need internet access in order to set up the Dymo printer.


Install the software as a Windows or Mac Administrator for all users to avoid permissions issues.

1. Install the Dymo Software

You will need to download and install Dymo Connect for Mac or Windows. Once that is installed, the last step of the installation process is to plug in the Dymo printer using the USB cord provided.


If you are using a LabelWriter 450 Turbo or Twin Turbo, already have the Dymo Label Software installed, and are not on Windows 11, you can continue without installing Dymo Connect. If you upgrade to Windows 11, you will need to uninstall the Dymo Label Software and install the Dymo Connect software instead.

Once it's installed, open the Dymo software and select Print at the bottom right of the screen to make sure the printer is working with your computer. If it doesn't print, try restarting your computer and/or reinstalling the software from the website.

You'll also want to make sure the word "Dymo" is in the name of your printer on your Printers Page so that Check-Ins can find it.

Dymo Twin Turbo Users Only

Make sure your software is on the following versions:

  • Check-Ins App: v1.9.2 (Download Here)

  • Check-Ins Printing: v2.1.4+ (Mac Download, Windows Download)

  • Java: Adoptium [Eclipse Temurin v 17+] (choose your OS version and architecture, JDK, and version 17 in the filters to see the correct download option) (Download Here)


    Adoptium v17 will only work if you have also updated Check-Ins Printing app to v2.1.4+

After updating those applications on each of your printing stations, restart those devices.

2. Create a Station

You will use the Check-Ins Printing App to print to the Dymo printer.

If you haven't already, create a new Check-Ins station.

The Check-Ins Printing App can be found in the System Tray. This must be running and not blocked for Check-Ins to print to the Dymo printer.

To make sure your printer is working correctly, send a test print to the printer.

  1. From the Check-Ins app menu, go to Window > Printer Check.

  2. Click Send Test Print.

  3. If you're using custom labels, click Test Custom Labels, and then click Send Test Print on the next page.

  4. The label will print.


If your labels are printing in the wrong orientation, check the Rotate print 90˚ box from the Printer Check page.


Check-Ins Printing App

We don't have direct access to the hardware on your computer. In order to gain access, we need to use either a plugin or widget of some sort that can communicate and translate our code to the printer. Our printing widget is called the Check-Ins Printing App.

  1. Download the latest Check-Ins App which comes with the Check-Ins Printing App.

  2. Install and open the Check-Ins app.


    If using Windows, make sure to right-click and select "Run as Administrator"

  3. Select 'Remember this decision' and then tap Allow, when prompted for the Check-Ins Printing App.


Printing App Troubleshooting

If you are seeing this message, you may need to follow the steps below to delete the printing app's certificate from your computer and reconfigure the permissions.

  1. Look for the Check-Ins Printing App in your System Tray or Menu bar. It looks like a box with a checkmark in it. It might be in your hidden icons.

  2. Tap the Check-Ins Printing app icon, and then select Advanced Site Manager in the drop-down menu

  3. In the Site Manager modal, select the Blocked tab and delete any entries

  4. Select the Allowed tab and delete the Planning Center entry and any other entries

  5. Tap Close, and then restart the Check-Ins app

  6. Check Remember this decision and then tap Allow


If you do not see this prompt, or tap the Remember this decision the first time, you will need to follow the steps above to delete the current certificate and get the prompt again.


If the printer isn't working properly, first try to unplug the power cord from the printer, wait 10 sections, and then plug it back in. If the cord feels loose, you might need a new printer or USB-C.

If unplugging doesn't work, the next option is to go through a Clean Install.


Before you try the other steps, verify you are using the Windows/Mac Check-Ins App instead of using a browser station.

When you install the app, it creates a new Check-Ins Station, so you may need to update station templates that pointed to your old browser station.

We created the Windows/Mac app to avoid issues with browser updates blocking communication between Check-Ins and the Dymo Web Service.

If your issue isn't listed here, chat with other people in our Slack Community or contact support using the ? in the app.

Clean Install

  1. Unplug the printer from the computer.

  2. From the Printers & Scanners page, delete any print jobs in the Printer Queue.

  3. Delete the Dymo Label Software or Dymo Connect (Applications folder on Mac, Program Files folder on Windows), empty your Trash, AND delete the printer from the Printers & Scanners page.

  4. Complete any pending computer updates.

  5. Reboot the computer.

  6. Download and install the latest version of Dymo Connect as an admin on your computer. You will be prompted on the final step to plug in the printer.

  7. Reboot the computer.

  8. Make sure there is only a single Dymo Label printer listed and that it is set to be your default printer.

  9. Open Dymo Connect and try a test print.

  10. Launch the Check-Ins App. The Check-Ins Printing App should be showing with other open applications. It's a checkmark icon.

  11. Check in someone who should print a label.


Rebooting your computer both times is the key, so please do not skip those steps.


Windows: If you're having trouble removing the Dymo software from your computer, contact Planning Center Support for assistance.

Update Drivers/Software

Make sure all your apps are up to date! Here are links to the minimum required versions of all the applications you will need for printing to work:

  • Latest version of Dymo Connect (Download Here)

  • Check-ins App: v1.9.2 (Download Here)

  • Check-ins Printing: v2.1.4+ (Mac Download, Windows Download)

  • Java: Adoptium [Eclipse Temurin v 17+] (choose your OS version and architecture, JDK, and version 17 in the filters to see the correct download option) (Download Here)


    Adoptium v17 will only work if you have also updated Check-Ins Printing app to v2.1.4+

  • After installing any updated versions, make sure to restart your computer.

Multiple Printers Installed

Go to Devices and Printers in the Control Panel (Windows) or System Preferences (Mac). Make sure there is only one instance of the Dymo printer installed, and that it's set to be your default printer.

If you have multiple Dymo printers installed, you will need to move the inactive one. To figure out which one that is:

  1. Unplug your Dymo printer from the computer.

  2. Right click the one that did not become greyed out when you unplugged the printer.

  3. Select Remove Device (Windows) or click the minus button (-) on the bottom right (Mac).

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