Error -1044 happens intermittently at the end of flashing and loading up at the start of a debug session. Sometimes it does load and I am debug from .out file and even with error it seems the flash worked. I videoed a loading debug session and failing session and will include screenshot here. The issue is the following error that suspends the debug session appears in the console window:
C28xx_CPU1: Trouble Halting Target CPU: (Error -1135 @ 0x80000) The debug probe reported an error. Confirm debug probe configuration and connections, reset the debug probe, and retry the operation. (Emulation package 9.4.0.00129)
C28xx_CPU1: Unable to determine target status after 20 attempts
C28xx_CPU1: Breakpoint Manager: Unable to remove requested AET job
C28xx_CPU1: Breakpoint Manager: Unable to remove requested AET job
C28xx_CPU1: Failed to remove the debug state from the target before disconnecting. There may still be breakpoint op-codes embedded in program memory. It is recommended that you reset the emulator before you connect and reload your program before you continue debugging
Texas Instruments XDS110 USB Debug Probe_0/CPU1_CLA1 : Target must be connected before loading program.
