Hi Rob Yu ,
Your ota_bootloader is stuck, it is caused by you lack the lwip_httpssrv_ota_freertos, the jumpt to function will jump to lwip_httpssrv_ota_freertos.
So,
1. Download the evkmimxrt1060_ota_bootloader, build the release version.
2. Download the evkmimxrt1060_lwip_httpssrv_ota_freertos
Means you enter the debug mode, then exit, just download the code is OK.

You don't need to debug it.
ota_bootloader and the lwip_httpssrv_ota_freertros are in the different flash location:


After you download the two code, please press the on board reset button.
Please also note, SW7 is: 1-off,2-off,3-on,4-off, just select the internal boot mode.
Please use my method download the two code again:
1, evkmimxrt1060_ota_bootloader, enter debug mode, exit it.
2. evkmimxrt1060_lwip_httpssrv_ota_freertos enter debug mode, exit it.
3. press on board reset
4. check the uart printf log
5. ping 192.168.0.102
Then all the other steps, please check my last reply.
Please check the code function works or not at first, not just debug it, even you debug it, you also need to debug evkmimxrt1060_lwip_httpssrv_ota_freertos , not the evkmimxrt1060_ota_bootloader, as evkmimxrt1060_ota_bootloader code will jump to evkmimxrt1060_lwip_httpssrv_ota_freertos, and run it.
Please try it again.
If you still have questions, please tell me which IDE version you are using? I am using MCUXpresso IDE v11.1.0 [Build 3209] [2019-12-12]
Let's make the windows version works at first, if your colleague Linux version still have issue, I will help him after your windows version works.
If you still have questions about it, please kindly let me know.
Kerry
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