$ openocd -f esp32s2_saola.cfg
Open On-Chip Debugger v0.10.0-esp32-20210401-13-g5d011fa5 (2021-05-12-12:41)
Licensed under GNU GPL v2
For bug reports, read
http://openocd.org/doc/doxygen/bugs.html
adapter speed: 3000 kHz

Info : Listening on port 6666 for tcl connections
Info : Listening on port 4444 for telnet connections
Info : clock speed 3000 kHz
Info : JTAG tap: esp32s2.cpu tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32s2: Target halted, PC=0x40000400, debug_reason=00000000
Info : Detected ESP32-S2 chip
Info : Listening on port 3333 for gdb connections
Info : accepting 'gdb' connection on tcp/3333
Warn : No symbols for FreeRTOS!
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Error: Failed to get flash maps (-6)!
Warn : Application image is invalid! Check configured binary flash offset 'appimage_offset'.
Warn : Failed to get flash mappings (-4)!
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Info : Auto-detected flash bank 'esp32s2.flash' size 4096 KB
Info : Using flash bank 'esp32s2.flash' size 4096 KB
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Error: Failed to get flash maps (-6)!
Warn : Application image is invalid! Check configured binary flash offset 'appimage_offset'.
Warn : Failed to get flash mappings (-4)!
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Info : Using flash bank 'esp32s2.irom' size 0 KB
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Error: Failed to get flash maps (-6)!
Warn : Application image is invalid! Check configured binary flash offset 'appimage_offset'.
Warn : Failed to get flash mappings (-4)!
Info : esp32s2: Target halted, PC=0x40031CAA, debug_reason=00000001
Info : Using flash bank 'esp32s2.drom' size 0 KB
Warn : negative reply, retrying
Warn : RTOS FreeRTOS not detected. (GDB could not find symbol 'pxCurrentTCB')
Warn : RTOS FreeRTOS not detected. (GDB could not find symbol 'pxCurrentTCB')
Warn : RTOS FreeRTOS not detected. (GDB could not find symbol 'pxCurrentTCB')
invalid command name "nuttx.pid_offset"
invalid command name "nuttx.xcpreg_offset"
invalid command name "nuttx.state_offset"
invalid command name "nuttx.name_offset"
invalid command name "nuttx.name_size"
Info : JTAG tap: esp32s2.cpu tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32s2: Debug controller was reset.
Info : esp32s2: Core was reset.
Info : esp32s2: Target halted, PC=0x40007299, debug_reason=00000000
Info : esp32s2: Core was reset.
Info : esp32s2: Target halted, PC=0x40000400, debug_reason=00000000
Info : JTAG tap: esp32s2.cpu tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32s2: Debug controller was reset.
Info : esp32s2: Core was reset.
Info : esp32s2: Target halted, PC=0x4000F99B, debug_reason=00000000
Info : esp32s2: Core was reset.
Info : esp32s2: Target halted, PC=0x40000400, debug_reason=00000000
Warn : address 0x400804b0 not writable
Error: esp32s2: Failed to write breakpoint instruction (-4)!
Error: esp32s2: Failed to add SW breakpoint!
Error: can't add breakpoint: unknown reason

In another terminal execute:

$ xtensa-esp32-elf-gdb nuttx
GNU gdb (crosstool-NG esp-2020r2) 8.1.0.20180627-git
Copyright (C) 2018 Free Software Foundation, Inc.
…
Reading symbols from nuttx…done.

(gdb) target extended-remote :3333
Remote debugging using :3333
0x4001276f in ?? ()

(gdb) symbol-file nuttx
Load new symbol table from "nuttx"? (y or n) y
Reading symbols from nuttx…done.
invalid command name "nuttx.pid_offset"
invalid command name "nuttx.xcpreg_offset"
invalid command name "nuttx.state_offset"
invalid command name "nuttx.name_offset"
invalid command name "nuttx.name_size"

(gdb) set remote hardware-watchpoint-limit 2

(gdb) mon reset halt
JTAG tap: esp32s2.cpu tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
esp32s2: Debug controller was reset.
esp32s2: Core was reset.
esp32s2: Target halted, PC=0x40007299, debug_reason=00000000
esp32s2: Core was reset.
esp32s2: Target halted, PC=0x40000400, debug_reason=00000000

(gdb) flushregs
Register cache flushed.

(gdb) b __start
Breakpoint 1 at 0x400226b8: file chip/esp32s2_start.c, line 77.

(gdb) b nx_start
Breakpoint 2 at 0x400804b0: file init/nx_start.c, line 353.

(gdb) run
The program being debugged has been started already.
Start it from the beginning? (y or n) y
Starting program: /comum/workspace/Espressif/NuttX/nuttx/nuttx
Warning:
Cannot insert breakpoint 2.
Cannot access memory at address 0x400804b0

Command aborted.

(gdb) c
Continuing.
Warning:
Cannot insert breakpoint 2.
Cannot access memory at address 0x400804b0

Command aborted.
(gdb)