diff --git a/include/asterisk/channel.h b/include/asterisk/channel.h
index 55604694c5..2814fac942 100644
--- a/include/asterisk/channel.h
+++ b/include/asterisk/channel.h
@@ -608,6 +608,7 @@ enum {
 	AST_FEATURE_PARKCALL =     (1 << 5),
 	AST_FEATURE_AUTOMIXMON =   (1 << 6),
 	AST_FEATURE_NO_H_EXTEN =   (1 << 7),
+	AST_FEATURE_WARNING_ACTIVE = (1 << 7),
 };
 
 /*! \brief bridge configuration */
@@ -615,6 +616,7 @@ struct ast_bridge_config {
 	struct ast_flags features_caller;
 	struct ast_flags features_callee;
 	struct timeval start_time;
+	struct timeval nexteventts;
 	long feature_timer;
 	long timelimit;
 	long play_warning;
diff --git a/main/channel.c b/main/channel.c
index e03ed21090..a57f64925d 100644
--- a/main/channel.c
+++ b/main/channel.c
@@ -4359,10 +4359,13 @@ static enum ast_bridge_result ast_generic_bridge(struct ast_channel *c0, struct
 		if (bridge_end.tv_sec) {
 			to = ast_tvdiff_ms(bridge_end, ast_tvnow());
 			if (to <= 0) {
-				if (config->timelimit)
+				if (config->timelimit) {
 					res = AST_BRIDGE_RETRY;
-				else
+					/* generic bridge ending to play warning */
+					ast_set_flag(config, AST_FEATURE_WARNING_ACTIVE);
+				} else {
 					res = AST_BRIDGE_COMPLETE;
+				}
 				break;
 			}
 		} else
@@ -4441,6 +4444,7 @@ static enum ast_bridge_result ast_generic_bridge(struct ast_channel *c0, struct
 				ast_debug(1, "Got DTMF %s on channel (%s)\n", 
 					f->frametype == AST_FRAME_DTMF_END ? "end" : "begin",
 					who->name);
+
 				break;
 			}
 			/* Write immediately frames, not passed through jb */
@@ -4512,7 +4516,6 @@ enum ast_bridge_result ast_channel_bridge(struct ast_channel *c0, struct ast_cha
 	int o0nativeformats;
 	int o1nativeformats;
 	long time_left_ms=0;
-	struct timeval nexteventts = { 0, };
 	char caller_warning = 0;
 	char callee_warning = 0;
 
@@ -4559,11 +4562,11 @@ enum ast_bridge_result ast_channel_bridge(struct ast_channel *c0, struct ast_cha
 	o1nativeformats = c1->nativeformats;
 
 	if (config->feature_timer) {
-		nexteventts = ast_tvadd(config->start_time, ast_samp2tv(config->feature_timer, 1000));
-	} else if (config->timelimit) {
-		nexteventts = ast_tvadd(config->start_time, ast_samp2tv(config->timelimit, 1000));
+		config->nexteventts = ast_tvadd(config->start_time, ast_samp2tv(config->feature_timer, 1000));
+	} else if (config->timelimit && firstpass) {
+		config->nexteventts = ast_tvadd(config->start_time, ast_samp2tv(config->timelimit, 1000));
 		if (caller_warning || callee_warning)
-			nexteventts = ast_tvsub(nexteventts, ast_samp2tv(config->play_warning, 1000));
+			config->nexteventts = ast_tvsub(config->nexteventts, ast_samp2tv(config->play_warning, 1000));
 	}
 
 	if (!c0->tech->send_digit_begin)
@@ -4582,9 +4585,9 @@ enum ast_bridge_result ast_channel_bridge(struct ast_channel *c0, struct ast_cha
 
 		to = -1;
 
-		if (!ast_tvzero(nexteventts)) {
+		if (!ast_tvzero(config->nexteventts)) {
 			now = ast_tvnow();
-			to = ast_tvdiff_ms(nexteventts, now);
+			to = ast_tvdiff_ms(config->nexteventts, now);
 			if (to <= 0) {
 				if (!config->timelimit) {
 					res = AST_BRIDGE_COMPLETE;
@@ -4612,7 +4615,7 @@ enum ast_bridge_result ast_channel_bridge(struct ast_channel *c0, struct ast_cha
 			}
 			
 			if (!to) {
-				if (time_left_ms >= 5000 && config->warning_sound && config->play_warning) {
+				if (time_left_ms >= 5000 && config->warning_sound && config->play_warning && ast_test_flag(config, AST_FEATURE_WARNING_ACTIVE)) {
 					int t = (time_left_ms + 500) / 1000; /* round to nearest second */
 					if (caller_warning)
 						bridge_playfile(c0, c1, config->warning_sound, t);
@@ -4620,10 +4623,11 @@ enum ast_bridge_result ast_channel_bridge(struct ast_channel *c0, struct ast_cha
 						bridge_playfile(c1, c0, config->warning_sound, t);
 				}
 				if (config->warning_freq && (time_left_ms > (config->warning_freq + 5000)))
-					nexteventts = ast_tvadd(nexteventts, ast_samp2tv(config->warning_freq, 1000));
+					config->nexteventts = ast_tvadd(config->nexteventts, ast_samp2tv(config->warning_freq, 1000));
 				else
-					nexteventts = ast_tvadd(config->start_time, ast_samp2tv(config->timelimit, 1000));
+					config->nexteventts = ast_tvadd(config->start_time, ast_samp2tv(config->timelimit, 1000));
 			}
+			ast_clear_flag(config, AST_FEATURE_WARNING_ACTIVE);
 		}
 
 		if (c0->_softhangup == AST_SOFTHANGUP_UNBRIDGE || c1->_softhangup == AST_SOFTHANGUP_UNBRIDGE) {
@@ -4726,9 +4730,13 @@ enum ast_bridge_result ast_channel_bridge(struct ast_channel *c0, struct ast_cha
 		if (!ast_strlen_zero(pbx_builtin_getvar_helper(c1, "BRIDGEPEER")))
 			pbx_builtin_setvar_helper(c1, "BRIDGEPEER", c0->name);
 
-		res = ast_generic_bridge(c0, c1, config, fo, rc, nexteventts);
-		if (res != AST_BRIDGE_RETRY)
+		res = ast_generic_bridge(c0, c1, config, fo, rc, config->nexteventts);
+		if (res != AST_BRIDGE_RETRY) {
+			break;
+		} else if (config->feature_timer) {
+			/* feature timer expired but has not been updated, sending to ast_bridge_call to do so */
 			break;
+		}
 	}
 
 	ast_clear_flag(c0, AST_FLAG_END_DTMF_ONLY);
diff --git a/main/features.c b/main/features.c
index d1dfcba7f6..9ae81865e5 100644
--- a/main/features.c
+++ b/main/features.c
@@ -2267,6 +2267,15 @@ int ast_bridge_call(struct ast_channel *chan,struct ast_channel *peer,struct ast
 		if (config->feature_timer) {
 			/* Update time limit for next pass */
 			diff = ast_tvdiff_ms(ast_tvnow(), config->start_time);
+			if (res == AST_BRIDGE_RETRY) {
+				/* The feature fully timed out but has not been updated. Skip
+				 * the potential round error from the diff calculation and
+				 * explicitly set to expired. */
+				config->feature_timer = -1;
+			} else {
+				config->feature_timer -= diff;
+			}
+
 			config->feature_timer -= diff;
 			if (hasfeatures) {
 				/* Running on backup config, meaning a feature might be being