diff --git a/src/sysupdate/sysupdated.c b/src/sysupdate/sysupdated.c
index e8f4ffd1d5..6f15177c94 100644
--- a/src/sysupdate/sysupdated.c
+++ b/src/sysupdate/sysupdated.c
@@ -210,7 +210,7 @@ static int job_parse_child_output(int _fd, sd_json_variant **ret) {
         assert(ret);
 
         if (fstat(fd, &st) < 0)
-                return log_error_errno(errno, "Failed to stat stdout fd: %m");
+                return log_debug_errno(errno, "Failed to stat stdout fd: %m");
 
         assert(S_ISREG(st.st_mode));
 
@@ -220,15 +220,15 @@ static int job_parse_child_output(int _fd, sd_json_variant **ret) {
         }
 
         if (lseek(fd, SEEK_SET, 0) == (off_t) -1)
-                return log_error_errno(errno, "Failed to seek to beginning of memfd: %m");
+                return log_debug_errno(errno, "Failed to seek to beginning of memfd: %m");
 
         f = take_fdopen(&fd, "r");
         if (!f)
-                return log_error_errno(errno, "Failed to reopen memfd: %m");
+                return log_debug_errno(errno, "Failed to reopen memfd: %m");
 
         r = sd_json_parse_file(f, "stdout", 0, &v, NULL, NULL);
         if (r < 0)
-                return log_error_errno(r, "Failed to parse JSON: %m");
+                return log_debug_errno(r, "Failed to parse JSON: %m");
 
         *ret = TAKE_PTR(v);
         return 0;
@@ -248,6 +248,8 @@ static void job_on_ready(Job *j) {
         if (!j->detach_cb)
                 return;
 
+        log_debug("Got READY=1 from job %" PRIu64", detaching.", j->id);
+
         assert(j->dbus_msg);
         msg = TAKE_PTR(j->dbus_msg);
 
@@ -255,7 +257,7 @@ static void job_on_ready(Job *j) {
 
         r = j->detach_cb(msg, j);
         if (r < 0)
-                log_warning_errno(r, "Failed to run callback on job ready event, ignoring: %m");
+                log_warning_errno(r, "Failed to detach job %" PRIu64 ", ignoring: %m", j->id);
 }
 
 static void job_on_errno(Job *j, const char *buf) {
@@ -266,7 +268,7 @@ static void job_on_errno(Job *j, const char *buf) {
 
         r = parse_errno(buf);
         if (r < 0) {
-                log_warning_errno(r, "Got invalid errno value, ignoring: %m");
+                log_warning_errno(r, "Got invalid errno value from job %" PRIu64 ", ignoring: %m", j->id);
                 return;
         }
 
@@ -336,7 +338,7 @@ static int job_on_exit(sd_event_source *s, const siginfo_t *si, void *userdata)
         else {
                 r = job_parse_child_output(TAKE_FD(j->stdout_fd), &json);
                 if (r < 0)
-                        sd_bus_error_set_errnof(&error, r, "Failed to parse JSON: %m");
+                        sd_bus_error_set_errnof(&error, r, "Failed to parse job worker output: %m");
         }
 
         /* Only send notification of exit if the job was actually detached */
@@ -351,17 +353,23 @@ static int job_on_exit(sd_event_source *s, const siginfo_t *si, void *userdata)
                                 j->object_path,
                                 j->status_errno != 0 ? -j->status_errno : si->si_status);
                 if (r < 0)
-                        log_warning_errno(r, "Cannot emit JobRemoved message, ignoring: %m");
+                        log_warning_errno(r,
+                                          "Cannot emit JobRemoved message for job %" PRIu64 ", ignoring: %m",
+                                          j->id);
         }
 
         if (j->dbus_msg && j->complete_cb) {
                 if (sd_bus_error_is_set(&error)) {
-                        log_warning("Bus error occurred, ignoring callback for job: %s", error.message);
+                        log_warning("Job %" PRIu64 " failed with bus error, ignoring callback: %s",
+                                    j->id, error.message);
                         sd_bus_reply_method_error(j->dbus_msg, &error);
                 } else {
                         r = j->complete_cb(j->dbus_msg, j, json, &error);
                         if (r < 0) {
-                                log_warning_errno(r, "Error during execution of job callback: %s", bus_error_message(&error, r));
+                                log_warning_errno(r,
+                                                  "Error during execution of job callback for job %" PRIu64 ": %s",
+                                                  j->id,
+                                                  bus_error_message(&error, r));
                                 sd_bus_reply_method_errno(j->dbus_msg, r, &error);
                         }
                 }
@@ -506,6 +514,9 @@ static int job_start(Job *j) {
                 _exit(EXIT_FAILURE);
         }
 
+        log_info("Started job %" PRIu64 " with worker PID " PID_FMT,
+                 j->id, pid.pid);
+
         r = event_add_child_pidref(j->manager->event, &j->child, &pid, WEXITED, job_on_exit, j);
         if (r < 0)
                 return log_error_errno(r, "Failed to add child process to event loop: %m");