diff --git a/daemon/logger/journald/read.go b/daemon/logger/journald/read.go
index 65afdfa5c8..992108b8c3 100644
--- a/daemon/logger/journald/read.go
+++ b/daemon/logger/journald/read.go
@@ -17,7 +17,10 @@ import (
 	"github.com/docker/docker/daemon/logger/journald/internal/sdjournal"
 )
 
-const closedDrainTimeout = 5 * time.Second
+const (
+	closedDrainTimeout = 5 * time.Second
+	waitInterval       = 250 * time.Millisecond
+)
 
 // Fields which we know are not user-provided attribute fields.
 var wellKnownFields = map[string]bool{
@@ -46,13 +49,13 @@ var wellKnownFields = map[string]bool{
 }
 
 type reader struct {
-	s           *journald
-	j           *sdjournal.Journal
-	logWatcher  *logger.LogWatcher
-	config      logger.ReadConfig
-	maxOrdinal  uint64
-	initialized bool
-	ready       chan struct{}
+	s             *journald
+	j             *sdjournal.Journal
+	logWatcher    *logger.LogWatcher
+	config        logger.ReadConfig
+	maxOrdinal    uint64
+	ready         chan struct{}
+	drainDeadline time.Time
 }
 
 func getMessage(d map[string]string) (line []byte, ok bool) {
@@ -103,89 +106,155 @@ func getAttrs(d map[string]string) []backend.LogAttr {
 // no more log entries to send to the log watcher.
 var errDrainDone = errors.New("journald drain done")
 
-// drainJournal reads and sends log messages from the journal.
-//
-// drainJournal returns errDrainDone when a terminal stopping condition has been
-// reached: the watch consumer is gone, a log entry is read which has a
-// timestamp after until (if until is nonzero), or the log driver is closed and
-// the last message logged has been sent from the journal. If the end of the
-// journal is reached without encountering a terminal stopping condition, a nil
-// error is returned.
-func (r *reader) drainJournal() error {
-	if !r.initialized {
-		defer func() {
-			r.signalReady()
-			r.initialized = true
-		}()
+// The SeekXYZ() methods all move the journal read pointer to a "conceptual"
+// position which does not correspond to any journal entry. A subsequent call to
+// Next(), Previous() or similar is necessary to resolve the read pointer to a
+// discrete entry.
+// https://github.com/systemd/systemd/pull/5930#issuecomment-300878104
+// But that's not all! If there is no discrete entry to resolve the position to,
+// the call to Next() or Previous() will just leave the read pointer in a
+// conceptual position, or do something even more bizarre.
+// https://github.com/systemd/systemd/issues/9934
 
-		var (
-			err          error
-			seekedToTail bool
-		)
-		if r.config.Tail >= 0 {
-			if r.config.Until.IsZero() {
-				err = r.j.SeekTail()
-				seekedToTail = true
-			} else {
-				err = r.j.SeekRealtime(r.config.Until)
-			}
-		} else {
-			if r.config.Since.IsZero() {
-				err = r.j.SeekHead()
-			} else {
-				err = r.j.SeekRealtime(r.config.Since)
-			}
-		}
-		if err != nil {
-			return err
-		}
+// initialSeekHead positions the journal read pointer at the earliest journal
+// entry with a timestamp of at least r.config.Since. It returns true if there
+// is an entry to read at the read pointer.
+func (r *reader) initialSeekHead() (bool, error) {
+	var err error
+	if r.config.Since.IsZero() {
+		err = r.j.SeekHead()
+	} else {
+		err = r.j.SeekRealtime(r.config.Since)
+	}
+	if err != nil {
+		return false, err
+	}
+	return r.j.Next()
+}
 
-		// SeekTail() followed by Next() behaves incorrectly, so we need
-		// to work around the bug by ensuring the first discrete
-		// movement of the read pointer is Previous() or PreviousSkip().
-		// PreviousSkip() is called inside the loop when config.Tail > 0
-		// so the only special case requiring special handling is
-		// config.Tail == 0.
-		// https://github.com/systemd/systemd/issues/9934
-		if seekedToTail && r.config.Tail == 0 {
-			// Resolve the read pointer to the last entry in the
-			// journal so that the call to Next() inside the loop
-			// advances past it.
-			if ok, err := r.j.Previous(); err != nil || !ok {
-				return err
-			}
-		}
+// initialSeekTail positions the journal read pointer at a journal entry
+// relative to the tail of the journal at the time of the call based on the
+// specification in r.config. It returns true if there is an entry to read at
+// the read pointer. Otherwise the read pointer is set to a conceptual position
+// which will be resolved to the desired entry (once written) by advancing
+// forward with r.j.Next() or similar.
+func (r *reader) initialSeekTail() (bool, error) {
+	var err error
+	if r.config.Until.IsZero() {
+		err = r.j.SeekTail()
+	} else {
+		err = r.j.SeekRealtime(r.config.Until)
+	}
+	if err != nil {
+		return false, err
 	}
 
-	for i := 0; ; i++ {
-		if !r.initialized && i == 0 && r.config.Tail > 0 {
-			if n, err := r.j.PreviousSkip(uint(r.config.Tail)); err != nil || n == 0 {
-				return err
+	var ok bool
+	if r.config.Tail == 0 {
+		ok, err = r.j.Previous()
+	} else {
+		var n int
+		n, err = r.j.PreviousSkip(uint(r.config.Tail))
+		ok = n > 0
+	}
+	if err != nil {
+		return ok, err
+	}
+	if !ok {
+		// The (filtered) journal has no entries. The tail is the head: all new
+		// entries which get written into the journal from this point forward
+		// should be read from the journal. However the read pointer is
+		// positioned at a conceptual position which is not condusive to reading
+		// those entries. The tail of the journal is resolved to the last entry
+		// in the journal _at the time of the first successful Previous() call_,
+		// which means that an arbitrary number of journal entries added in the
+		// interim may be skipped: race condition. While the realtime conceptual
+		// position is not so racy, it is also unhelpful: it is the timestamp
+		// past where reading should stop, so all logs that should be followed
+		// would be skipped over.
+		// Reset the read pointer position to avoid these problems.
+		return r.initialSeekHead()
+	} else if r.config.Tail == 0 {
+		// The journal read pointer is positioned at the discrete position of
+		// the journal entry _before_ the entry to send.
+		return r.j.Next()
+	}
+
+	// Check if the PreviousSkip went too far back.
+	timestamp, err := r.j.Realtime()
+	if err != nil {
+		return false, err
+	}
+	if timestamp.Before(r.config.Since) {
+		if err := r.j.SeekRealtime(r.config.Since); err != nil {
+			return false, err
+		}
+		return r.j.Next()
+	}
+	return true, nil
+}
+
+// wait blocks until the journal has new data to read, the reader's drain
+// deadline is exceeded, or the log reading consumer is gone.
+func (r *reader) wait() (sdjournal.Status, error) {
+	for {
+		dur := waitInterval
+		if !r.drainDeadline.IsZero() {
+			dur = time.Until(r.drainDeadline)
+			if dur < 0 {
+				// Container is gone but we haven't found the end of the
+				// logs before the deadline. Maybe it was dropped by
+				// journald, e.g. due to rate-limiting.
+				return sdjournal.StatusNOP, errDrainDone
+			} else if dur > waitInterval {
+				dur = waitInterval
 			}
-		} else if ok, err := r.j.Next(); err != nil || !ok {
+		}
+		status, err := r.j.Wait(dur)
+		if err != nil || status != sdjournal.StatusNOP {
+			return status, err
+		}
+		select {
+		case <-r.logWatcher.WatchConsumerGone():
+			return status, errDrainDone
+		case <-r.s.closed:
+			// Container is gone; don't wait indefinitely for journal entries that will never arrive.
+			if r.drainDeadline.IsZero() {
+				r.drainDeadline = time.Now().Add(closedDrainTimeout)
+			}
+		default:
+		}
+	}
+}
+
+// nextWait blocks until there is a new journal entry to read, and advances the
+// journal read pointer to it.
+func (r *reader) nextWait() error {
+	for {
+		if ok, err := r.j.Next(); err != nil || ok {
 			return err
 		}
-
-		if !r.initialized && i == 0 {
-			// The cursor is in a position which will be unaffected
-			// by subsequent logging.
-			r.signalReady()
+		if _, err := r.wait(); err != nil {
+			return err
 		}
+	}
+}
 
+// drainJournal reads and sends log messages from the journal, starting from the
+// current read pointer, until the end of the journal or a terminal stopping
+// condition is reached.
+//
+// errDrainDone is returned when a terminal stopping condition has been
+// reached: the watch consumer is gone, a log entry is read which has a
+// timestamp after until (if until is nonzero), or the log driver is closed and
+// the last message logged has been sent from the journal.
+func (r *reader) drainJournal() error {
+	for i := 0; ; i++ {
 		// Read the entry's timestamp.
 		timestamp, err := r.j.Realtime()
 		if err != nil {
 			return err
 		}
-		// Check if the PreviousSkip went too far back. Check only the
-		// initial position as we are comparing wall-clock timestamps,
-		// which may not be monotonic. We don't want to skip over
-		// messages sent later in time just because the clock moved
-		// backwards.
-		if !r.initialized && i == 0 && r.config.Tail > 0 && timestamp.Before(r.config.Since) {
-			r.j.SeekRealtime(r.config.Since)
-			continue
-		}
 		if !r.config.Until.IsZero() && r.config.Until.Before(timestamp) {
 			return errDrainDone
 		}
@@ -243,6 +312,10 @@ func (r *reader) drainJournal() error {
 					Warn("journald: error processing journal")
 			}
 		}
+
+		if ok, err := r.j.Next(); err != nil || !ok {
+			return err
+		}
 	}
 }
 
@@ -255,28 +328,15 @@ func (r *reader) readJournal() error {
 		return nil
 	}
 
-	var drainDeadline time.Time
 	if !r.config.Follow {
 		if r.s.readSyncTimeout == 0 {
 			return nil
 		}
-		drainDeadline = time.Now().Add(r.s.readSyncTimeout)
+		r.drainDeadline = time.Now().Add(r.s.readSyncTimeout)
 	}
 
 	for {
-		if !drainDeadline.IsZero() && time.Now().After(drainDeadline) {
-			// Container is gone but we haven't found the end of the
-			// logs within the timeout. Maybe it was dropped by
-			// journald, e.g. due to rate-limiting.
-			return nil
-		}
-		status, err := r.j.Wait(250 * time.Millisecond)
-		if err != nil {
-			return err
-		}
 		select {
-		case <-r.logWatcher.WatchConsumerGone():
-			return nil // won't be able to write anything anymore
 		case <-r.s.closed:
 			// container is gone, drain journal
 			lastSeq := atomic.LoadUint64(&r.s.ordinal)
@@ -284,17 +344,16 @@ func (r *reader) readJournal() error {
 				// All caught up with the logger!
 				return nil
 			}
-			if drainDeadline.IsZero() {
-				drainDeadline = time.Now().Add(closedDrainTimeout)
-			}
 		default:
-			if status == sdjournal.StatusNOP {
-				// no new data -- keep waiting
-				continue
-			}
 		}
-		err = r.drainJournal()
-		if err != nil {
+
+		if err := r.nextWait(); err != nil {
+			if err != errDrainDone {
+				return err
+			}
+			return nil
+		}
+		if err := r.drainJournal(); err != nil {
 			if err != errDrainDone {
 				return err
 			}
@@ -357,6 +416,33 @@ func (r *reader) readLogs() {
 		return
 	}
 
+	var ok bool
+	if r.config.Tail >= 0 {
+		ok, err = r.initialSeekTail()
+	} else {
+		ok, err = r.initialSeekHead()
+	}
+	if err != nil {
+		r.logWatcher.Err <- err
+		return
+	}
+	r.signalReady()
+	if !ok {
+		if !r.config.Follow {
+			return
+		}
+		// Either the read pointer is positioned at a discrete journal entry, in
+		// which case the position will be unaffected by subsequent logging, or
+		// the read pointer is in the conceptual position corresponding to the
+		// first journal entry to send once it is logged in the future.
+		if err := r.nextWait(); err != nil {
+			if err != errDrainDone {
+				r.logWatcher.Err <- err
+			}
+			return
+		}
+	}
+
 	if err := r.readJournal(); err != nil {
 		r.logWatcher.Err <- err
 		return