diff --git a/src/run-tests.pl b/src/run-tests.pl
index 6a12616..64c926a 100755
--- a/src/run-tests.pl
+++ b/src/run-tests.pl
@@ -941,6 +941,7 @@ sub test($$$$)
 
 my @x01 = (
   I, 0, I,
+  P, "_", "*", "_",
   R, "*", "", "",  # Skipped/failed messages to prevent maxuid topping
   S, "", "", "*",
   A, "*F", "*", "*",
@@ -949,6 +950,8 @@ my @x01 = (
   D, "*", "*", "*",
   E, "*T", "*", "*",
   F, "*", "*", "*T",
+  O, "*T", "*T", "*T",
+  Q, "_", "*T", "*T",
   G, "*F", "*", "_",
   H, "*FT", "*", "*",
   I, "_", "*", "*",
@@ -961,11 +964,13 @@ my @x01 = (
 my @O01 = ("", "", "");
 my @X01 = (
   M, 0, K,
+  P, "", "/", "",
   A, "", "+F", "+F",
   B, "+F", "+F", "",
   C, "", "+FS", "+S",
   E, "", "+T", "+T",
   F, "+T", "+T", "",
+  Q, "", "<", "",
   G, "+T", ">", "",
   H, "", "+FT", "+FT",
   I, "", "<", "+T",
@@ -979,11 +984,14 @@ test("full", \@x01, \@X01, \@O01);
 my @O02 = ("", "", "Expunge Both\n");
 my @X02 = (
   M, 0, K,
+  P, "", "/", "",
   A, "", "+F", "+F",
   B, "+F", "+F", "",
   C, "", "+FS", "+S",
   E, "/", "/", "/",
   F, "/", "/", "/",
+  O, "/", "/", "/",
+  Q, "", "/", "/",
   G, "/", "/", "",
   H, "/", "/", "/",
   I, "", "/", "/",
@@ -997,11 +1005,14 @@ test("full + expunge both", \@x01, \@X02, \@O02);
 my @O03 = ("", "", "Expunge Near\n");
 my @X03 = (
   M, 0, K,
+  P, "", "/", "",
   A, "", "+F", "+F",
   B, "+F", "+F", "",
   C, "", "+FS", "+S",
   E, "", ">+T", "/",
   F, "+T", ">+T", "/",
+  O, "", ">", "/",
+  Q, "", "/", "/",
   G, "+T", ">", "",
   H, "", ">+T", "/",
   I, "", "/", "/",
@@ -1014,9 +1025,11 @@ test("full + expunge near side", \@x01, \@X03, \@O03);
 my @O04 = ("", "", "Sync Pull\n");
 my @X04 = (
   K, 0, I,
+  P, "", "/", "",  # Only because test uses Maildir driver
   A, "", "+F", "+F",
   C, "", "+FS", "+S",
   E, "", "+T", "+T",
+  Q, "", "<", "",
   H, "", "+FT", "+FT",
   I, "", "<", "+T",
   J, "", "*T", "*T",
@@ -1027,11 +1040,13 @@ test("pull", \@x01, \@X04, \@O04);
 my @O05 = ("", "", "Sync Flags\n");
 my @X05 = (
   I, 0, I,
+  P, "", "/", "",
   A, "", "+F", "+F",
   B, "+F", "+F", "",
   C, "", "+FS", "+S",
   E, "", "+T", "+T",
   F, "+T", "+T", "",
+  Q, "", "<", "",
   H, "", "+FT", "+FT",
 );
 test("flags", \@x01, \@X05, \@O05);
@@ -1039,7 +1054,9 @@ test("flags", \@x01, \@X05, \@O05);
 my @O06 = ("", "", "Sync Delete\n");
 my @X06 = (
   I, 0, I,
+  P, "", "/", "",
   G, "+T", ">", "",
+  Q, "", "<", "",
   I, "", "<", "+T",
 );
 test("deletions", \@x01, \@X06, \@O06);
@@ -1057,9 +1074,11 @@ test("new", \@x01, \@X07, \@O07);
 my @O08 = ("", "", "Sync PushFlags PullDelete\n");
 my @X08 = (
   I, 0, I,
+  P, "", "/", "",
   B, "+F", "+F", "",
   C, "", "+F", "",
   F, "+T", "+T", "",
+  Q, "", "<", "",
   I, "", "<", "+T",
 );
 test("push flags + pull deletions", \@x01, \@X08, \@O08);
@@ -1067,8 +1086,11 @@ test("push flags + pull deletions", \@x01, \@X08, \@O08);
 my @O09 = ("", "", "Sync None\nExpunge Both\n");
 my @X09 = (
   I, 0, I,
+  P, "", "/", "",
   E, "/", "", "",
   F, "", "", "/",
+  O, "/", "/", "/",
+  Q, "", "/", "/",
   H, "/", "", "",
   J, "/", "", "",
   L, "", "", "/",
@@ -1080,6 +1102,8 @@ my @O0A = ("", "", "Sync None\nExpunge Near\n");
 my @X0A = (
   I, 0, I,
   F, "", "", "/",
+  O, "", "", "/",
+  Q, "", "", "/",
   L, "", "", "/",
 );
 test("noop + expunge near side", \@x01, \@X0A, \@O0A);
diff --git a/src/sync.c b/src/sync.c
index a2d4746..e52eed0 100644
--- a/src/sync.c
+++ b/src/sync.c
@@ -1036,6 +1036,7 @@ box_loaded( int sts, message_t *msgs, int total_msgs, int recent_msgs, void *aux
 				} else if (del[t]) {
 					// The target was newly expunged, so there is nothing to update.
 					// The deletion is propagated in the opposite iteration.
+					srec->status |= S_GONE(t);
 				} else if (!srec->uid[t]) {
 					// The target was never stored, or was previously expunged, so there
 					// is nothing to update.
@@ -1340,7 +1341,7 @@ box_loaded( int sts, message_t *msgs, int total_msgs, int recent_msgs, void *aux
 		for (t = 0; t < 2; t++) {
 			if (!srec->uid[t])
 				continue;
-			if (!srec->msg[t] && (svars->opts[t] & OPEN_OLD)) {
+			if (srec->status & S_GONE(t)) {
 				// The message was expunged. No need to call flags_set(), because:
 				// - for S_DELETE and S_PURGE, the entry will be pruned due to both sides being gone
 				// - for regular flag propagations, there is nothing to do
@@ -1571,10 +1572,7 @@ flags_set_p2( sync_vars_t *svars, sync_rec_t *srec, int t )
 	if (srec->status & S_PURGE) {
 		JLOG( "P %u %u", (srec->uid[F], srec->uid[N]), "deleted dummy" );
 		srec->status = (srec->status & ~S_PURGE) | S_PURGED;
-	} else if (srec->status & S_DELETE) {
-		JLOG( "%c %u %u 0", ("><"[t], srec->uid[F], srec->uid[N]), "%sed deletion", str_hl[t] );
-		srec->uid[t^1] = 0;
-	} else {
+	} else if (!(srec->status & S_DELETE)) {
 		uchar nflags = (srec->flags | srec->aflags[t]) & ~srec->dflags[t];
 		if (srec->flags != nflags) {
 			JLOG( "* %u %u %u", (srec->uid[F], srec->uid[N], nflags), "%sed flags %s; were %s",
@@ -1802,24 +1800,26 @@ box_closed_p2( sync_vars_t *svars, int t )
 			PC_JLOG( "N %d %u", (t, svars->maxuid[t]), "up maxuid of %s", str_fn[t] );
 	}
 
-	if (((svars->state[F] | svars->state[N]) & ST_DID_EXPUNGE) || svars->chan->max_messages) {
-		debug( "purging obsolete entries\n" );
-		for (srec = svars->srecs; srec; srec = srec->next) {
-			if (srec->status & S_DEAD)
-				continue;
-			if (!srec->uid[N] || ((srec->status & S_DEL(N)) && (svars->state[N] & ST_DID_EXPUNGE))) {
-				if (!srec->uid[F] || ((srec->status & S_DEL(F)) && (svars->state[F] & ST_DID_EXPUNGE)) ||
-				    ((srec->status & S_EXPIRED) && svars->maxuid[F] >= srec->uid[F] && svars->maxxfuid >= srec->uid[F])) {
-					PC_JLOG( "- %u %u", (srec->uid[F], srec->uid[N]), "killing" );
-					srec->status = S_DEAD;
-				} else if (srec->uid[N] && (srec->status & S_DEL(F))) {
-					PC_JLOG( "> %u %u 0", (srec->uid[F], srec->uid[N]), "orphaning" );
-					srec->uid[N] = 0;
-				}
-			} else if (srec->uid[F] && ((srec->status & S_DEL(F)) && (svars->state[F] & ST_DID_EXPUNGE)) && (srec->status & S_DEL(N))) {
-				PC_JLOG( "< %u %u 0", (srec->uid[F], srec->uid[N]), "orphaning" );
-				srec->uid[F] = 0;
+	debug( "purging obsolete entries\n" );
+	for (srec = svars->srecs; srec; srec = srec->next) {
+		if (srec->status & S_DEAD)
+			continue;
+		if ((srec->status & S_DEL(F)) && (svars->state[F] & ST_DID_EXPUNGE))
+			srec->status |= S_GONE(F);
+		if ((srec->status & S_DEL(N)) && (svars->state[N] & ST_DID_EXPUNGE))
+			srec->status |= S_GONE(N);
+		if (!srec->uid[N] || (srec->status & S_GONE(N))) {
+			if (!srec->uid[F] || (srec->status & S_GONE(F)) ||
+				((srec->status & S_EXPIRED) && svars->maxuid[F] >= srec->uid[F] && svars->maxxfuid >= srec->uid[F])) {
+				PC_JLOG( "- %u %u", (srec->uid[F], srec->uid[N]), "killing" );
+				srec->status = S_DEAD;
+			} else if (srec->uid[N] && (srec->status & S_DEL(F))) {
+				PC_JLOG( "> %u %u 0", (srec->uid[F], srec->uid[N]), "orphaning" );
+				srec->uid[N] = 0;
 			}
+		} else if (srec->uid[F] && (srec->status & S_GONE(F)) && (srec->status & S_DEL(N))) {
+			PC_JLOG( "< %u %u 0", (srec->uid[F], srec->uid[N]), "orphaning" );
+			srec->uid[F] = 0;
 		}
 	}
 
diff --git a/src/sync_p.h b/src/sync_p.h
index 9e79830..45fcd3c 100644
--- a/src/sync_p.h
+++ b/src/sync_p.h
@@ -17,6 +17,7 @@ BIT_ENUM(
 	S_PENDING,      // the entry is new and awaits propagation (possibly a retry)
 	S_DUMMY(2),     // f/n message is only a placeholder
 	S_SKIPPED,      // pre-1.4 legacy: the entry was not propagated (message is too big)
+	S_GONE(2),      // ephemeral: f/n message has been expunged
 	S_DEL(2),       // ephemeral: f/n message would be subject to expunge
 	S_DELETE,       // ephemeral: flags propagation is a deletion
 	S_UPGRADE,      // ephemeral: upgrading placeholder, do not apply MaxSize