diff --git a/src/journal/journalctl.c b/src/journal/journalctl.c
index e79acc65bc..de1534befd 100644
--- a/src/journal/journalctl.c
+++ b/src/journal/journalctl.c
@@ -2164,10 +2164,12 @@ static int setup_event(Context *c, int fd, sd_event **ret) {
 }
 
 static int run(int argc, char *argv[]) {
-        bool need_seek = false, since_seeked = false, use_cursor = false, after_cursor = false;
+        bool need_seek = false, since_seeked = false, after_cursor = false;
         _cleanup_(loop_device_unrefp) LoopDevice *loop_device = NULL;
         _cleanup_(umount_and_freep) char *mounted_dir = NULL;
         _cleanup_(sd_journal_closep) sd_journal *j = NULL;
+        _cleanup_free_ char *cursor_from_file = NULL;
+        const char *cursor = NULL;
         int n_shown, r, poll_fd = -EBADF;
 
         setlocale(LC_ALL, "");
@@ -2444,8 +2446,7 @@ static int run(int argc, char *argv[]) {
         }
 
         if (arg_cursor || arg_after_cursor || arg_cursor_file) {
-                _cleanup_free_ char *cursor_from_file = NULL;
-                const char *cursor = arg_cursor ?: arg_after_cursor;
+                cursor = arg_cursor ?: arg_after_cursor;
 
                 if (arg_cursor_file) {
                         r = read_one_line_file(arg_cursor_file, &cursor_from_file);
@@ -2458,30 +2459,40 @@ static int run(int argc, char *argv[]) {
                         }
                 } else
                         after_cursor = arg_after_cursor;
-
-                if (cursor) {
-                        r = sd_journal_seek_cursor(j, cursor);
-                        if (r < 0)
-                                return log_error_errno(r, "Failed to seek to cursor: %m");
-
-                        use_cursor = true;
-                }
         }
 
-        if (use_cursor) {
-                if (!arg_reverse)
-                        r = sd_journal_next_skip(j, 1 + after_cursor);
-                else
-                        r = sd_journal_previous_skip(j, 1 + after_cursor);
+        if (cursor) {
+                r = sd_journal_seek_cursor(j, cursor);
+                if (r < 0)
+                        return log_error_errno(r, "Failed to seek to cursor: %m");
 
-                if (after_cursor && r < 2) {
+                r = sd_journal_step_one(j, !arg_reverse);
+                if (r < 0)
+                        return log_error_errno(r, "Failed to iterate through journal: %m");
+
+                if (after_cursor && r > 0) {
+                        /* With --after-cursor=/--cursor-file= we want to skip the first entry only if it's
+                         * the entry the cursor is pointing at, otherwise, if some journal filters are used,
+                         * we might skip the first entry of the filter match, which leads to unexpectedly
+                         * missing journal entries. */
+                        int k;
+
+                        k = sd_journal_test_cursor(j, cursor);
+                        if (k < 0)
+                                return log_error_errno(k, "Failed to test cursor against current entry: %m");
+                        if (k > 0)
+                                /* Current entry matches the one our cursor is pointing at, so let's try
+                                 * to advance the next entry. */
+                                r = sd_journal_step_one(j, !arg_reverse);
+                }
+
+                if (r == 0) {
                         /* We couldn't find the next entry after the cursor. */
                         if (arg_follow)
                                 need_seek = true;
                         else
                                 arg_lines = 0;
                 }
-
         } else if (arg_until_set && (arg_reverse || arg_lines_needs_seek_end())) {
                 /* If both --until and any of --reverse and --lines=N is specified, things get
                  * a little tricky. We seek to the place of --until first. If only --reverse or
diff --git a/test/units/testsuite-04.journal.sh b/test/units/testsuite-04.journal.sh
index 3efac616e0..4d9e48717a 100755
--- a/test/units/testsuite-04.journal.sh
+++ b/test/units/testsuite-04.journal.sh
@@ -241,3 +241,27 @@ diff -u /tmp/lb1 - <<'EOF'
 [{"index":-3,"boot_id":"5ea5fc4f82a14186b5332a788ef9435e","first_entry":1666569600994371,"last_entry":1666584266223608},{"index":-2,"boot_id":"bea6864f21ad4c9594c04a99d89948b0","first_entry":1666569601005945,"last_entry":1666584347230411},{"index":-1,"boot_id":"4c708e1fd0744336be16f3931aa861fb","first_entry":1666569601017222,"last_entry":1666584354649355},{"index":0,"boot_id":"35e8501129134edd9df5267c49f744a4","first_entry":1666569601009823,"last_entry":1666584438086856}]
 EOF
 rm -rf "$JOURNAL_DIR" /tmp/lb1
+
+# Check that using --after-cursor/--cursor-file= together with journal filters doesn't
+# skip over entries matched by the filter
+# See: https://github.com/systemd/systemd/issues/30288
+UNIT_NAME="test-cursor-$RANDOM.service"
+CURSOR_FILE="$(mktemp)"
+# Generate some messages we can match against
+journalctl --cursor-file="$CURSOR_FILE" -n1
+systemd-run --unit="$UNIT_NAME" --wait --service-type=exec bash -xec "echo hello; echo world"
+journalctl --sync
+# --after-cursor= + --unit=
+# The format of the "Starting ..." message depends on StatusUnitFormat=, so match only the beginning
+# which should be enough in this case
+[[ "$(journalctl -n 1 -p info -o cat --unit="$UNIT_NAME" --after-cursor="$(<"$CURSOR_FILE")" _PID=1 )" =~ ^Starting\  ]]
+# There should be no such messages before the cursor
+[[ -z "$(journalctl -n 1 -p info -o cat --unit="$UNIT_NAME" --after-cursor="$(<"$CURSOR_FILE")" --reverse)" ]]
+# --cursor-file= + a journal filter
+diff <(journalctl --cursor-file="$CURSOR_FILE" -p info -o cat _SYSTEMD_UNIT="$UNIT_NAME") - <<EOF
++ echo hello
+hello
++ echo world
+world
+EOF
+rm -f "$CURSOR_FILE"