diff --git a/src/journal/journald-server.c b/src/journal/journald-server.c
index 56f2ea8583..0ff6a43e5b 100644
--- a/src/journal/journald-server.c
+++ b/src/journal/journald-server.c
@@ -667,6 +667,33 @@ void server_rotate(Server *s) {
         server_process_deferred_closes(s);
 }
 
+static void server_rotate_journal(Server *s, ManagedJournalFile *f, uid_t uid) {
+        int r;
+
+        assert(s);
+        assert(f);
+
+        /* This is similar to server_rotate(), but rotates only specified journal file.
+         *
+         * 💣💣💣 This invalidate 'f', and the caller cannot reuse the passed JournalFile object. 💣💣💣 */
+
+        if (f == s->system_journal)
+                (void) do_rotate(s, &s->system_journal, "system", s->seal, /* uid= */ 0);
+        else if (f == s->runtime_journal)
+                (void) do_rotate(s, &s->runtime_journal, "runtime", /* seal= */ false, /* uid= */ 0);
+        else {
+                assert(ordered_hashmap_get(s->user_journals, UID_TO_PTR(uid)) == f);
+                r = do_rotate(s, &f, "user", s->seal, uid);
+                if (r >= 0)
+                        ordered_hashmap_replace(s->user_journals, UID_TO_PTR(uid), f);
+                else if (!f)
+                        /* Old file has been closed and deallocated */
+                        ordered_hashmap_remove(s->user_journals, UID_TO_PTR(uid));
+        }
+
+        server_process_deferred_closes(s);
+}
+
 void server_sync(Server *s) {
         ManagedJournalFile *f;
         int r;
@@ -819,7 +846,7 @@ static bool shall_try_append_again(JournalFile *f, int r) {
 }
 
 static void write_to_journal(Server *s, uid_t uid, struct iovec *iovec, size_t n, int priority) {
-        bool vacuumed = false, rotate = false;
+        bool vacuumed = false;
         struct dual_timestamp ts;
         ManagedJournalFile *f;
         int r;
@@ -841,23 +868,25 @@ static void write_to_journal(Server *s, uid_t uid, struct iovec *iovec, size_t n
                  * bisection works correctly. */
 
                 log_info("Time jumped backwards, rotating.");
-                rotate = true;
-        } else {
+                server_rotate(s);
+                server_vacuum(s, /* verbose = */ false);
+                vacuumed = true;
+        }
 
-                f = find_journal(s, uid);
-                if (!f)
-                        return;
+        f = find_journal(s, uid);
+        if (!f)
+                return;
 
-                if (journal_file_rotate_suggested(f->file, s->max_file_usec, LOG_DEBUG)) {
-                        log_debug("%s: Journal header limits reached or header out-of-date, rotating.",
-                                  f->file->path);
-                        rotate = true;
+        if (journal_file_rotate_suggested(f->file, s->max_file_usec, LOG_DEBUG)) {
+                if (vacuumed) {
+                        log_warning("Suppressing rotation, as we already rotated immediately before write attempt. Giving up.");
+                        return;
                 }
-        }
 
-        if (rotate) {
-                server_rotate(s);
-                server_vacuum(s, false);
+                log_debug("%s: Journal header limits reached or header out-of-date, rotating.", f->file->path);
+
+                server_rotate_journal(s, TAKE_PTR(f), uid);
+                server_vacuum(s, /* verbose = */ false);
                 vacuumed = true;
 
                 f = find_journal(s, uid);
@@ -883,8 +912,8 @@ static void write_to_journal(Server *s, uid_t uid, struct iovec *iovec, size_t n
         else
                 log_ratelimit_full_errno(LOG_INFO, r, "Failed to write entry to %s (%zu items, %zu bytes), rotating before retrying: %m", f->file->path, n, IOVEC_TOTAL_SIZE(iovec, n));
 
-        server_rotate(s);
-        server_vacuum(s, false);
+        server_rotate_journal(s, TAKE_PTR(f), uid);
+        server_vacuum(s, /* verbose = */ false);
 
         f = find_journal(s, uid);
         if (!f)
@@ -1211,10 +1240,10 @@ int server_flush_to_var(Server *s, bool require_flag_file) {
 
                 log_info("Rotating system journal.");
 
-                server_rotate(s);
-                server_vacuum(s, false);
+                server_rotate_journal(s, s->system_journal, /* uid = */ 0);
+                server_vacuum(s, /* verbose = */ false);
 
-                if (!s->system_journal) {
+                if (!s->system_journal->file) {
                         log_notice("Didn't flush runtime journal since rotation of system journal wasn't successful.");
                         r = -EIO;
                         goto finish;