diff --git a/src/resolve/resolved-dns-query.c b/src/resolve/resolved-dns-query.c
index 58a7b2d878..7eb6b9736e 100644
--- a/src/resolve/resolved-dns-query.c
+++ b/src/resolve/resolved-dns-query.c
@@ -586,7 +586,7 @@ void dns_query_complete(DnsQuery *q, DnsTransactionState state) {
 
         q->state = state;
 
-        (void) manager_monitor_send(q->manager, q->state, q->answer_rcode, q->answer_errno, q->question_idna, q->question_utf8, q->collected_questions, q->answer);
+        (void) manager_monitor_send(q->manager, q->state, q->answer_rcode, q->answer_errno, q->question_idna, q->question_utf8, q->question_bypass, q->collected_questions, q->answer);
 
         dns_query_stop(q);
         if (q->complete)
diff --git a/src/resolve/resolved-manager.c b/src/resolve/resolved-manager.c
index fd800cedfe..fc8d7412fb 100644
--- a/src/resolve/resolved-manager.c
+++ b/src/resolve/resolved-manager.c
@@ -1105,6 +1105,7 @@ int manager_monitor_send(
                 int error,
                 DnsQuestion *question_idna,
                 DnsQuestion *question_utf8,
+                DnsPacket *question_bypass,
                 DnsQuestion *collected_questions,
                 DnsAnswer *answer) {
 
@@ -1119,11 +1120,22 @@ int manager_monitor_send(
         if (set_isempty(m->varlink_subscription))
                 return 0;
 
-        /* Merge both questions format into one */
+        /* Merge all questions into one */
         r = dns_question_merge(question_idna, question_utf8, &merged);
         if (r < 0)
                 return log_error_errno(r, "Failed to merge UTF8/IDNA questions: %m");
 
+        if (question_bypass) {
+                _cleanup_(dns_question_unrefp) DnsQuestion *merged2 = NULL;
+
+                r = dns_question_merge(merged, question_bypass->question, &merged2);
+                if (r < 0)
+                        return log_error_errno(r, "Failed to merge UTF8/IDNA questions and DNS packet question: %m");
+
+                dns_question_unref(merged);
+                merged = TAKE_PTR(merged2);
+        }
+
         /* Convert the current primary question to JSON */
         r = dns_question_to_json(merged, &jquestion);
         if (r < 0)
diff --git a/src/resolve/resolved-manager.h b/src/resolve/resolved-manager.h
index 16b883bd21..5cd5e834d3 100644
--- a/src/resolve/resolved-manager.h
+++ b/src/resolve/resolved-manager.h
@@ -176,7 +176,7 @@ int manager_start(Manager *m);
 
 uint32_t manager_find_mtu(Manager *m);
 
-int manager_monitor_send(Manager *m, int state, int rcode, int error, DnsQuestion *question_idna, DnsQuestion *question_utf8, DnsQuestion *collected_questions, DnsAnswer *answer);
+int manager_monitor_send(Manager *m, int state, int rcode, int error, DnsQuestion *question_idna, DnsQuestion *question_utf8, DnsPacket *question_bypass, DnsQuestion *collected_questions, DnsAnswer *answer);
 
 int manager_write(Manager *m, int fd, DnsPacket *p);
 int manager_send(Manager *m, int fd, int ifindex, int family, const union in_addr_union *destination, uint16_t port, const union in_addr_union *source, DnsPacket *p);
diff --git a/test/units/testsuite-75.sh b/test/units/testsuite-75.sh
index 7e73d2e952..b34045fcb5 100755
--- a/test/units/testsuite-75.sh
+++ b/test/units/testsuite-75.sh
@@ -40,7 +40,7 @@ monitor_check_rr() (
     # displayed. We turn off pipefail for this, since we don't care about the
     # lhs of this pipe expression, we only care about the rhs' result to be
     # clean
-    timeout -v 30s journalctl -u resmontest.service --since "$since" -f --full | grep -m1 "$match"
+    timeout -v 30s journalctl -u resolvectl-monitor.service --since "$since" -f --full | grep -m1 "$match"
 )
 
 # Test for resolvectl, resolvconf
@@ -238,7 +238,8 @@ resolvectl status
 resolvectl log-level debug
 
 # Start monitoring queries
-systemd-run -u resmontest.service -p Type=notify resolvectl monitor
+systemd-run -u resolvectl-monitor.service -p Type=notify resolvectl monitor
+systemd-run -u resolvectl-monitor-json.service -p Type=notify resolvectl monitor --json=short
 
 # Check if all the zones are valid (zone-check always returns 0, so let's check
 # if it produces any errors/warnings)
@@ -529,7 +530,25 @@ grep -qF "fd00:dead:beef:cafe::123" "$RUN_OUT"
 #run dig +dnssec this.does.not.exist.untrusted.test
 #grep -qF "status: NXDOMAIN" "$RUN_OUT"
 
-systemctl stop resmontest.service
+# Issue: https://github.com/systemd/systemd/issues/29580 (part #1)
+dig @127.0.0.54 signed.test
+
+systemctl stop resolvectl-monitor.service
+systemctl stop resolvectl-monitor-json.service
+
+# Issue: https://github.com/systemd/systemd/issues/29580 (part #2)
+#
+# Check for any warnings regarding malformed messages
+(! journalctl -u resolvectl-monitor.service -u reseolvectl-monitor-json.service -p warning --grep malformed)
+# Verify that all queries recorded by `resolvectl monitor --json` produced a valid JSON
+# with expected fields
+journalctl -p info -o cat _SYSTEMD_UNIT="resolvectl-monitor-json.service" | while read -r line; do
+    # Check that both "question" and "answer" fields are arrays
+    #
+    # The expression is slightly more complicated due to the fact that the "answer" field is optional,
+    # so we need to select it only if it's present, otherwise the type == "array" check would fail
+    echo "$line" | jq -e '[. | .question, (select(has("answer")) | .answer) | type == "array"] | all'
+done
 
 # Test serve stale feature and NFTSet= if nftables is installed
 if command -v nft >/dev/null; then