Seeduino XIAO Error Help

Hey everyone. I have two Seeduino XIAO nrf boards and one I have been actively using for a while uploading code and having it work. After a few weeks of not touching the board I came back and now neither the board I used regularly nor the untouched one will accept code uploads.
They return this error text no matter what I upload (I'm using the blink sketch because it is simple):

Upgrading target on COM11 with DFU package C:\Users\jorda\AppData\Local\Temp\arduino_build_162596\Blink.ino.zip. Flow control is disabled, Single bank, Touch disabled
Timed out waiting for acknowledgement from device.

Failed to upgrade target. Error is: No data received on serial port. Not able to proceed.
Traceback (most recent call last):
  File "nordicsemi\__main__.py", line 294, in serial
  File "nordicsemi\dfu\dfu.py", line 235, in dfu_send_images
  File "nordicsemi\dfu\dfu.py", line 200, in _dfu_send_image
  File "nordicsemi\dfu\dfu_transport_serial.py", line 179, in send_start_dfu
  File "nordicsemi\dfu\dfu_transport_serial.py", line 243, in send_packet
  File "nordicsemi\dfu\dfu_transport_serial.py", line 282, in get_ack_nr
nordicsemi.exceptions.NordicSemiException: No data received on serial port. Not able to proceed.

Possible causes:
- Selected Bootloader version does not match the one on Bluefruit device.
    Please upgrade the Bootloader or select correct version in Tools->Bootloader.
- Baud rate must be 115200, Flow control must be off.
- Target is not in DFU mode. Ground DFU pin and RESET and release both to enter DFU mode.

Does anyone know what could be wrong? I looked around online and saw something about bootloaders but I don't understand how to two boards can separately just stop working like this.

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