diff --git a/src/isync.h b/src/isync.h
index 17e43ca..d27d42a 100644
--- a/src/isync.h
+++ b/src/isync.h
@@ -118,7 +118,6 @@ typedef struct group_conf {
 #define M_RECENT       (1<<0) /* unsyncable flag; maildir_* depend on this being 1<<0 */
 #define M_DEAD         (1<<1) /* expunged */
 #define M_FLAGS        (1<<2) /* flags fetched */
-#define M_EXPIRE       (1<<3) /* kicked out by MaxMessages */
 
 typedef struct message {
 	struct message *next;
diff --git a/src/sync.c b/src/sync.c
index bb8fa94..0f76e25 100644
--- a/src/sync.c
+++ b/src/sync.c
@@ -79,17 +79,21 @@ make_flags( int flags, char *buf )
 }
 
 #define S_DEAD         (1<<0)
-#define S_EXPIRED      (1<<1)
+#define S_DONE         (1<<1)
 #define S_DEL(ms)      (1<<(2+(ms)))
-#define S_EXP_S        (1<<4)
-#define S_DONE         (1<<6)
+#define S_EXPIRED      (1<<4)
+#define S_EXPIRE       (1<<5)
+#define S_NEXPIRE      (1<<6)
+#define S_EXP_S        (1<<7)
+
+#define mvBit(in,ib,ob) ((unsigned char)(((unsigned)in) * (ob) / (ib)))
 
 typedef struct sync_rec {
 	struct sync_rec *next;
 	/* string_list_t *keywords; */
 	int uid[2];
 	message_t *msg[2];
-	unsigned char flags, status;
+	unsigned char status, flags, aflags[2], dflags[2];
 } sync_rec_t;
 
 static void
@@ -186,11 +190,11 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 	char *dname, *jname, *nname, *lname, *s, *cmname, *csname;
 	FILE *dfp, *jfp, *nfp;
 	int opts[2];
-	int nom, nos, del[2], ex[2];
+	int nom, nos, del[2], ex[2], nex;
 	int muidval, suidval, smaxxuid, maxuid[2], minwuid, maxwuid;
 	int t1, t2, t3, t, uid, nmsgs;
-	int lfd, ret, line, sline, todel, delt, *mexcs, nmexcs, rmexcs;
-	unsigned char nflags;
+	int lfd, ret, line, sline, todel, *mexcs, nmexcs, rmexcs;
+	unsigned char nflags, sflags, aflags, dflags;
 	msg_data_t msgdata;
 	struct stat st;
 	struct flock lck;
@@ -291,7 +295,7 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 			s = fbuf;
 			if (*s == 'X') {
 				s++;
-				srec->status = S_EXPIRED;
+				srec->status = S_EXPIRE | S_EXPIRED;
 			} else
 				srec->status = 0;
 			srec->flags = parse_flags( s );
@@ -337,7 +341,7 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 				}
 				if (buf[0] == '(' || buf[0] == ')' ?
 				        (sscanf( buf + 2, "%d", &t1 ) != 1) :
-				    buf[0] == '-' || buf[0] == '|' ?
+				    buf[0] == '-' || buf[0] == '|' || buf[0] == '/' || buf[0] == '\\' ?
 					(sscanf( buf + 2, "%d %d", &t1, &t2 ) != 2) :
 					(sscanf( buf + 2, "%d %d %d", &t1, &t2, &t3 ) != 3))
 				{
@@ -395,10 +399,26 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 						srec->flags = t3;
 						break;
 					case '~':
-						debug( "expired now %d\n", t3 );
+						debug( "expire now %d\n", t3 );
+						if (t3)
+							srec->status |= S_EXPIRE;
+						else
+							srec->status &= ~S_EXPIRE;
+						break;
+					case '\\':
+						t3 = (srec->status & S_EXPIRED);
+						debug( "expire back to %d\n", t3 / S_EXPIRED );
+						if (t3)
+							srec->status |= S_EXPIRE;
+						else
+							srec->status &= ~S_EXPIRE;
+						break;
+					case '/':
+						t3 = (srec->status & S_EXPIRE);
+						debug( "expired now %d\n", t3 / S_EXPIRE );
 						if (t3) {
-							if (smaxxuid < t2)
-								smaxxuid = t2;
+							if (smaxxuid < srec->uid[S])
+								smaxxuid = srec->uid[S];
 							srec->status |= S_EXPIRED;
 						} else
 							srec->status &= ~S_EXPIRED;
@@ -455,6 +475,12 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 	}
 	if ((chan->ops[S] & (OP_NEW|OP_RENEW)) && chan->max_messages)
 		opts[S] |= OPEN_OLD|OPEN_NEW|OPEN_FLAGS;
+	if (line)
+		for (srec = recs; srec; srec = srec->next)
+			if (!(srec->status & S_DEAD) && ((mvBit(srec->status, S_EXPIRE, S_EXPIRED) ^ srec->status) & S_EXPIRED)) {
+				opts[S] |= OPEN_OLD|OPEN_FLAGS;
+				break;
+			}
 	driver[M]->prepare_opts( ctx[M], opts[M] );
 	driver[S]->prepare_opts( ctx[S], opts[S] );
 
@@ -678,23 +704,18 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 		} else {
 			del[M] = nom && (srec->uid[M] > 0);
 			del[S] = nos && (srec->uid[S] > 0);
-			if (srec->msg[M] && (srec->msg[M]->flags & F_DELETED))
-				srec->status |= S_DEL(M);
-			if (srec->msg[S] && (srec->msg[S]->flags & F_DELETED))
-				srec->status |= S_DEL(S);
-			nflags = srec->flags;
 
 			for (t = 0; t < 2; t++) {
-				int unex;
-				unsigned char sflags, aflags, dflags;
-
+				srec->aflags[t] = srec->dflags[t] = 0;
+				if (srec->msg[t] && (srec->msg[t]->flags & F_DELETED))
+					srec->status |= S_DEL(t);
 				/* excludes (push) c.3) d.2) d.3) d.4) / (pull) b.3) d.7) d.8) d.9) */
 				if (!srec->uid[t]) {
 					/* b.1) / c.1) */
 					debug( "  no more %s\n", str_ms[t] );
 				} else if (del[1-t]) {
 					/* c.4) d.9) / b.4) d.4) */
-					if (srec->msg[t] && srec->msg[t]->flags != nflags)
+					if (srec->msg[t] && (srec->msg[t]->status & M_FLAGS) && srec->msg[t]->flags != srec->flags)
 						info( "Info: conflicting changes in (%d,%d)\n", srec->uid[M], srec->uid[S] );
 					if (chan->ops[t] & OP_DELETE) {
 						debug( "  %sing delete\n", str_hl[t] );
@@ -719,102 +740,125 @@ sync_boxes( store_t *ctx[], const char *names[], channel_conf_t *chan )
 					/* a) & b.3) / c.3) */
 					if (chan->ops[t] & OP_FLAGS) {
 						sflags = srec->msg[1-t]->flags;
-						aflags = sflags & ~nflags;
-						dflags = ~sflags & nflags;
-						unex = 0;
-						if (srec->status & S_EXPIRED) {
-							if (!t) {
-								if ((aflags & ~F_DELETED) || dflags)
-									info( "Info: Flags of expired message changed in (%d,%d)\n", srec->uid[M], srec->uid[S] );
-								continue;
-							} else {
-								if ((sflags & F_FLAGGED) && !(sflags & F_DELETED)) {
-									unex = 1;
-									dflags |= F_DELETED;
-								} else
-									continue;
-							}
-						}
-						if ((chan->ops[t] & OP_EXPUNGE) && (sflags & F_DELETED) &&
-						    (!ctx[t]->conf->trash || ctx[t]->conf->trash_only_new))
-						{
-							aflags &= F_DELETED;
-							dflags = 0;
-						}
+						if ((srec->status & (S_EXPIRE|S_EXPIRED)) && !t)
+							sflags &= ~F_DELETED;
+						srec->aflags[t] = sflags & ~srec->flags;
+						srec->dflags[t] = ~sflags & srec->flags;
 						if (DFlags & DEBUG) {
 							char afbuf[16], dfbuf[16]; /* enlarge when support for keywords is added */
-							make_flags( aflags, afbuf );
-							make_flags( dflags, dfbuf );
+							make_flags( srec->aflags[t], afbuf );
+							make_flags( srec->dflags[t], dfbuf );
 							debug( "  %sing flags: +%s -%s\n", str_hl[t], afbuf, dfbuf );
 						}
-						switch ((aflags | dflags) ? driver[t]->set_flags( ctx[t], srec->msg[t], srec->uid[t], aflags, dflags ) : DRV_OK) {
-						case DRV_STORE_BAD: ret = SYNC_BAD(t); goto finish;
-						case DRV_BOX_BAD: ret = SYNC_FAIL; goto finish;
-						default: /* ok */ break;
-						case DRV_OK:
-							if (aflags & F_DELETED)
-								srec->status |= S_DEL(t);
-							else if (dflags & F_DELETED)
-								srec->status &= ~S_DEL(t);
-							nflags = (nflags | aflags) & ~dflags;
-							if (unex) {
-								debug( "unexpiring pair(%d,%d)\n", srec->uid[M], srec->uid[S] );
-								/* log last, so deletion can't be misinterpreted! */
-								Fprintf( jfp, "~ %d %d 0\n", srec->uid[M], srec->uid[S] );
-								srec->status &= ~S_EXPIRED;
-							}
-						}
 					} else
 						debug( "  not %sing flags\n", str_hl[t] );
 				} /* else b.4) / c.4) */
 			}
-
-			if (srec->flags != nflags) {
-				debug( "  updating flags (%u -> %u)\n", srec->flags, nflags );
-				srec->flags = nflags;
-				Fprintf( jfp, "* %d %d %u\n", srec->uid[M], srec->uid[S], nflags );
-			}
 		}
 	}
 
-	if ((chan->ops[S] & (OP_NEW|OP_RENEW)) && chan->max_messages) {
-		debug( "expiring excess entries\n" );
+	if ((chan->ops[S] & (OP_NEW|OP_RENEW|OP_FLAGS)) && chan->max_messages) {
+		/* Flagged and not yet synced messages older than the first not
+		 * expired message are not counted. */
 		todel = ctx[S]->count - chan->max_messages;
+		debug( "scheduling %d excess messages for expiration\n", todel );
 		for (tmsg = ctx[S]->msgs; tmsg && todel > 0; tmsg = tmsg->next)
-			if (!(tmsg->status & M_DEAD) && (tmsg->flags & F_DELETED))
+			if (!(tmsg->status & M_DEAD) && (srec = tmsg->srec) &&
+			    ((tmsg->flags | srec->aflags[S]) & ~srec->dflags[S] & F_DELETED) &&
+			    !(srec->status & (S_EXPIRE|S_EXPIRED)))
 				todel--;
-		delt = 0;
-		for (tmsg = ctx[S]->msgs; tmsg && todel > 0; tmsg = tmsg->next) {
-			if ((tmsg->status & M_DEAD) || (tmsg->flags & F_DELETED))
+		debug( "%d non-deleted excess messages\n", todel );
+		for (tmsg = ctx[S]->msgs; tmsg; tmsg = tmsg->next) {
+			if (tmsg->status & M_DEAD)
 				continue;
-			if ((tmsg->flags & F_FLAGGED) || !tmsg->srec || tmsg->srec->uid[M] <= 0) /* add M_DESYNCED? */
-				todel--;
-			else if (!(tmsg->status & M_RECENT)) {
-				tmsg->status |= M_EXPIRE;
-				delt++;
+			if (!(srec = tmsg->srec) || srec->uid[M] <= 0)
 				todel--;
+			else {
+				nflags = (tmsg->flags | srec->aflags[S]) & ~srec->dflags[S];
+				if (!(nflags & F_DELETED) || (srec->status & (S_EXPIRE|S_EXPIRED))) {
+					if (nflags & F_FLAGGED)
+						todel--;
+					else if (!(tmsg->status & M_RECENT) &&
+					         (todel > 0 ||
+					          ((srec->status & (S_EXPIRE|S_EXPIRED)) == (S_EXPIRE|S_EXPIRED)) ||
+					          ((srec->status & (S_EXPIRE|S_EXPIRED)) && (tmsg->flags & F_DELETED)))) {
+						srec->status |= S_NEXPIRE;
+						debug( "  pair(%d,%d)\n", srec->uid[M], srec->uid[S] );
+						todel--;
+					}
+				}
 			}
 		}
-		if (delt) {
-			for (srec = recs; srec; srec = srec->next) {
-				if (srec->status & (S_DEAD|S_EXPIRED))
-					continue;
-				if (srec->msg[S] && (srec->msg[S]->status & M_EXPIRE)) {
-					debug( "  expiring pair(%d,%d)\n", srec->uid[M], srec->uid[S] );
-					/* log first, so deletion can't be misinterpreted! */
-					Fprintf( jfp, "~ %d %d 1\n", srec->uid[M], srec->uid[S] );
-					if (smaxxuid < srec->uid[S])
-						smaxxuid = srec->uid[S];
-					srec->status |= S_EXPIRED;
-					switch (driver[S]->set_flags( ctx[S], srec->msg[S], 0, F_DELETED, 0 )) {
-					case DRV_STORE_BAD: ret = SYNC_BAD(S); goto finish;
-					case DRV_BOX_BAD: ret = SYNC_FAIL; goto finish;
-					default: /* ok */ break;
-					case DRV_OK: srec->status |= S_DEL(S);
+		debug( "%d excess messages remain\n", todel );
+		for (srec = recs; srec; srec = srec->next) {
+			if ((srec->status & (S_DEAD|S_DONE)) || !srec->msg[S])
+				continue;
+			nex = (srec->status / S_NEXPIRE) & 1;
+			if (nex != ((srec->status / S_EXPIRED) & 1)) {
+				if (nex != ((srec->status / S_EXPIRE) & 1)) {
+					Fprintf( jfp, "~ %d %d %d\n", srec->uid[M], srec->uid[S], nex );
+					debug( "  pair(%d,%d): %d (pre)\n", srec->uid[M], srec->uid[S], nex );
+					srec->status = (srec->status & ~S_EXPIRE) | (nex * S_EXPIRE);
+				} else
+					debug( "  pair(%d,%d): %d (pending)\n", srec->uid[M], srec->uid[S], nex );
+			}
+		}
+	}
+	debug( "synchronizing flags\n" );
+	for (srec = recs; srec != *osrecadd; srec = srec->next) {
+		if (srec->status & (S_DEAD|S_DONE))
+			continue;
+		for (t = 0; t < 2; t++) {
+			aflags = srec->aflags[t];
+			dflags = srec->dflags[t];
+			if (t && ((mvBit(srec->status, S_EXPIRE, S_EXPIRED) ^ srec->status) & S_EXPIRED)) {
+				if (srec->status & S_NEXPIRE)
+					aflags |= F_DELETED;
+				else
+					dflags |= F_DELETED;
+			}
+			if ((chan->ops[t] & OP_EXPUNGE) && (((srec->msg[t] ? srec->msg[t]->flags : 0) | aflags) & ~dflags & F_DELETED) &&
+			    (!ctx[t]->conf->trash || ctx[t]->conf->trash_only_new))
+			{
+				srec->aflags[t] &= F_DELETED;
+				aflags &= F_DELETED;
+				srec->dflags[t] = dflags = 0;
+			}
+			if (srec->msg[t] && (srec->msg[t]->status & M_FLAGS)) {
+				aflags &= ~srec->msg[t]->flags;
+				dflags &= srec->msg[t]->flags;
+			}
+			switch ((aflags | dflags) ? driver[t]->set_flags( ctx[t], srec->msg[t], srec->uid[t], aflags, dflags ) : DRV_OK) {
+			case DRV_STORE_BAD: ret = SYNC_BAD(t); goto finish;
+			case DRV_BOX_BAD: ret = SYNC_FAIL; goto finish;
+			default: /* ok */ srec->aflags[t] = srec->dflags[t] = 0; break;
+			case DRV_OK:
+				if (aflags & F_DELETED)
+					srec->status |= S_DEL(t);
+				else if (dflags & F_DELETED)
+					srec->status &= ~S_DEL(t);
+				if (t) {
+					nex = (srec->status / S_NEXPIRE) & 1;
+					if (nex != ((srec->status / S_EXPIRED) & 1)) {
+						if (nex && (smaxxuid < srec->uid[S]))
+							smaxxuid = srec->uid[S];
+						Fprintf( jfp, "/ %d %d\n", srec->uid[M], srec->uid[S] );
+						debug( "  pair(%d,%d): expired %d (commit)\n", srec->uid[M], srec->uid[S], nex );
+						srec->status = (srec->status & ~S_EXPIRED) | (nex * S_EXPIRED);
+					} else if (nex != ((srec->status / S_EXPIRE) & 1)) {
+						Fprintf( jfp, "\\ %d %d\n", srec->uid[M], srec->uid[S] );
+						debug( "  pair(%d,%d): expire %d (cancel)\n", srec->uid[M], srec->uid[S], nex );
+						srec->status = (srec->status & ~S_EXPIRE) | (nex * S_EXPIRE);
 					}
 				}
 			}
 		}
+		nflags = (srec->flags | srec->aflags[M] | srec->aflags[S]) & ~(srec->dflags[M] | srec->dflags[S]);
+		if (srec->flags != nflags) {
+			debug( "  pair(%d,%d): updating flags (%u -> %u)\n", srec->uid[M], srec->uid[S], srec->flags, nflags );
+			srec->flags = nflags;
+			Fprintf( jfp, "* %d %d %u\n", srec->uid[M], srec->uid[S], nflags );
+		}
 	}
 
 	for (t = 0; t < 2; t++) {