I have managed to get it working. I added/removed a few things to my ini after @maxgerhardt 's suggestions.
Here is my platformio.ini:
[env:teensy41]
platform = teensy
board = teensy41
framework = arduino
upload_protocol = custom
upload_flags =
-device
MIMXRT1062xxx6A
-speed
4000
-if
jtag
-jtagconf
-1,-1
-autoconnect
1
-NoGui
1
-CommanderScript
"upload.jlink"
upload_command = $PROJECT_PACKAGES_DIR\tool-jlink\JLink.exe $UPLOAD_FLAGS
debug_tool = custom
debug_server =
C:\Users\\\<user>\\.platformio\packages\tool-jlink\JLinkGDBServerCL.exe
-singlerun
-if
jtag
-select
USB
-device
MIMXRT1062xxx6A
-port
2331
-speed
4000
debug_port = localhost:2331
debug_init_cmds =
target extended-remote $DEBUG_PORT
with an upload.jlink file at the root of the project:
r
loadfile .pio\build\teensy41\firmware.hex
r
q
Thanks for helping @maxgerhardt
I’m still not sure what the underlying issue is, I doubt I will look into it much further but if a dev is interested I can work with them to figure it out.