diff --git a/src/run/run.c b/src/run/run.c
index 6754b80bcf3..e49e918b0fc 100644
--- a/src/run/run.c
+++ b/src/run/run.c
@@ -735,6 +735,10 @@ static int parse_argv(int argc, char *argv[]) {
                 return log_error_errno(SYNTHETIC_ERRNO(EINVAL),
                                        "--timer-property= has no effect without any other timer options.");
 
+        if (sd_json_format_enabled(arg_json_format_flags) && with_trigger)
+                return log_error_errno(SYNTHETIC_ERRNO(EINVAL),
+                                       "--json= is not compatible with path, socket or timer operations.");
+
         if (arg_wait) {
                 if (arg_no_block)
                         return log_error_errno(SYNTHETIC_ERRNO(EINVAL),
diff --git a/test/units/TEST-74-AUX-UTILS.run.sh b/test/units/TEST-74-AUX-UTILS.run.sh
index a5c79ddb72e..0619a8995f7 100755
--- a/test/units/TEST-74-AUX-UTILS.run.sh
+++ b/test/units/TEST-74-AUX-UTILS.run.sh
@@ -257,6 +257,7 @@ systemd-run --wait --machine=.host --pty true
 systemd-run --json=short true | jq . >/dev/null
 systemd-run --json=pretty true | jq . >/dev/null
 (! systemd-run --wait --pipe --json=short true)
+(! systemd-run --json=short --on-active=30s true)
 (! SHELL=/bin/false systemd-run --quiet --shell)
 
 (! systemd-run)