It works for me, printing to stderr in the nudged program, and printing to results.txt, on the tests/infloop program. Maybe try that from a drmemory build directory as a sanity check?
$ bin64/drmemory -- tests/infloop
~~Dr.M~~ Dr. Memory version 2.3.18344
starting
<received nudge mask=0x40000 id=0x00000000 arg=0x0000000000000000>
~~Dr.M~~
~~Dr.M~~ Error #1: LEAK 42 direct bytes 0x00007f47e3320fb0-0x00007f47e3320fda + 17 indirect bytes
~~Dr.M~~ # 0 replace_malloc [/home/bruening/drmemory/git/src/common/alloc_replace.c:2577]
~~Dr.M~~ # 1 foo [/home/bruening/drmemory/git/src/tests/infloop.c:85]
~~Dr.M~~ # 2 main [/home/bruening/drmemory/git/src/tests/infloop.c:112]
~~Dr.M~~
~~Dr.M~~ Error #2: LEAK 8 direct bytes 0x00007f47e3321040-0x00007f47e3321048 + 19 indirect bytes
~~Dr.M~~ # 0 replace_malloc [/home/bruening/drmemory/git/src/common/alloc_replace.c:2577]
~~Dr.M~~ # 1 foo [/home/bruening/drmemory/git/src/tests/infloop.c:89]
~~Dr.M~~ # 2 main [/home/bruening/drmemory/git/src/tests/infloop.c:112]
~~Dr.M~~
~~Dr.M~~ Error #3: LEAK 160 direct bytes 0x00007f47e33210b0-0x00007f47e3321150 + 0 indirect bytes
~~Dr.M~~ # 0 replace_malloc [/home/bruening/drmemory/git/src/common/alloc_replace.c:2577]
~~Dr.M~~ # 1 foo [/home/bruening/drmemory/git/src/tests/infloop.c:96]
~~Dr.M~~ # 2 main [/home/bruening/drmemory/git/src/tests/infloop.c:112]
~~Dr.M~~
~~Dr.M~~ ERRORS FOUND:
~~Dr.M~~ 0 unique, 0 total unaddressable access(es)
~~Dr.M~~ 0 unique, 0 total uninitialized access(es)
~~Dr.M~~ 0 unique, 0 total invalid heap argument(s)
~~Dr.M~~ 0 unique, 0 total warning(s)
~~Dr.M~~ 3 unique, 22 total, 3286 byte(s) of leak(s)
~~Dr.M~~ 0 unique, 0 total, 0 byte(s) of possible leak(s)
~~Dr.M~~ ERRORS IGNORED:
~~Dr.M~~ 13 unique, 16 total, 6634 byte(s) of still-reachable allocation(s)
~~Dr.M~~ (re-run with "-show_reachable" for details)
~~Dr.M~~ Details: /home/bruening/drmemory/git/build_x64_dbg/logs/DrMemory-infloop.118045.000/results.txt
===========================================================================
SUMMARY AFTER NUDGE #1:
Error #1: LEAK 42 direct bytes 0x00007f47e3320fb0-0x00007f47e3320fda + 17 indirect bytes
# 0 replace_malloc [/home/bruening/drmemory/git/src/common/alloc_replace.c:2577]
# 1 foo [/home/bruening/drmemory/git/src/tests/infloop.c:85]
# 2 main [/home/bruening/drmemory/git/src/tests/infloop.c:112]