diff --git a/src/libcharon/sa/ikev1/task_manager_v1.c b/src/libcharon/sa/ikev1/task_manager_v1.c
index b4944cfcb..00f5e6f05 100644
--- a/src/libcharon/sa/ikev1/task_manager_v1.c
+++ b/src/libcharon/sa/ikev1/task_manager_v1.c
@@ -199,6 +199,14 @@ struct private_task_manager_t {
 	 */
 	u_int retransmit_tries;
 
+	/**
+	 * Maximum number of tries possible with current retransmission settings
+	 * before overflowing the range of uint32_t, which we use for the timeout.
+	 * Note that UINT32_MAX milliseconds equal nearly 50 days, so that doesn't
+	 * make much sense without retransmit_limit anyway.
+	 */
+	u_int retransmit_tries_max;
+
 	/**
 	 * Retransmission timeout
 	 */
@@ -355,7 +363,7 @@ static status_t retransmit_packet(private_task_manager_t *this, uint32_t seqnr,
 							u_int mid, u_int retransmitted, array_t *packets)
 {
 	packet_t *packet;
-	uint32_t t, max_jitter;
+	uint32_t t = UINT32_MAX, max_jitter;
 
 	array_get(packets, 0, &packet);
 	if (retransmitted > this->retransmit_tries)
@@ -364,8 +372,12 @@ static status_t retransmit_packet(private_task_manager_t *this, uint32_t seqnr,
 		charon->bus->alert(charon->bus, ALERT_RETRANSMIT_SEND_TIMEOUT, packet);
 		return DESTROY_ME;
 	}
-	t = (uint32_t)(this->retransmit_timeout * 1000.0 *
-					pow(this->retransmit_base, retransmitted));
+	if (this->retransmit_tries_max &&
+		retransmitted <= this->retransmit_tries_max)
+	{
+		t = (uint32_t)(this->retransmit_timeout * 1000.0 *
+						pow(this->retransmit_base, retransmitted));
+	}
 	if (this->retransmit_limit)
 	{
 		t = min(t, this->retransmit_limit);
@@ -2141,5 +2153,11 @@ task_manager_v1_t *task_manager_v1_create(ike_sa_t *ike_sa)
 	}
 	this->dpd_send &= 0x7FFFFFFF;
 
+	if (this->retransmit_base > 1)
+	{	/* based on 1000 * timeout * base^try */
+		this->retransmit_tries_max = log(UINT32_MAX/
+										 (1000.0 * this->retransmit_timeout))/
+									 log(this->retransmit_base);
+	}
 	return &this->public;
 }
diff --git a/src/libcharon/sa/ikev2/task_manager_v2.c b/src/libcharon/sa/ikev2/task_manager_v2.c
index 09b824a75..6e1d00851 100644
--- a/src/libcharon/sa/ikev2/task_manager_v2.c
+++ b/src/libcharon/sa/ikev2/task_manager_v2.c
@@ -150,6 +150,14 @@ struct private_task_manager_t {
 	 */
 	u_int retransmit_tries;
 
+	/**
+	 * Maximum number of tries possible with current retransmission settings
+	 * before overflowing the range of uint32_t, which we use for the timeout.
+	 * Note that UINT32_MAX milliseconds equal nearly 50 days, so that doesn't
+	 * make much sense without retransmit_limit anyway.
+	 */
+	u_int retransmit_tries_max;
+
 	/**
 	 * Retransmission timeout
 	 */
@@ -331,7 +339,7 @@ METHOD(task_manager_t, retransmit, status_t,
 	if (message_id == this->initiating.mid &&
 		array_count(this->initiating.packets))
 	{
-		uint32_t timeout, max_jitter;
+		uint32_t timeout = UINT32_MAX, max_jitter;
 		job_t *job;
 		enumerator_t *enumerator;
 		packet_t *packet;
@@ -357,22 +365,7 @@ METHOD(task_manager_t, retransmit, status_t,
 
 		if (!mobike || !mobike->is_probing(mobike))
 		{
-			if (this->initiating.retransmitted <= this->retransmit_tries)
-			{
-				timeout = (uint32_t)(this->retransmit_timeout * 1000.0 *
-					pow(this->retransmit_base, this->initiating.retransmitted));
-
-				if (this->retransmit_limit)
-				{
-					timeout = min(timeout, this->retransmit_limit);
-				}
-				if (this->retransmit_jitter)
-				{
-					max_jitter = (timeout / 100.0) * this->retransmit_jitter;
-					timeout -= max_jitter * (random() / (RAND_MAX + 1.0));
-				}
-			}
-			else
+			if (this->initiating.retransmitted > this->retransmit_tries)
 			{
 				DBG1(DBG_IKE, "giving up after %d retransmits",
 					 this->initiating.retransmitted - 1);
@@ -380,7 +373,21 @@ METHOD(task_manager_t, retransmit, status_t,
 								   packet);
 				return DESTROY_ME;
 			}
-
+			if (this->retransmit_tries_max &&
+				this->initiating.retransmitted <= this->retransmit_tries_max)
+			{
+				timeout = (uint32_t)(this->retransmit_timeout * 1000.0 *
+					pow(this->retransmit_base, this->initiating.retransmitted));
+			}
+			if (this->retransmit_limit)
+			{
+				timeout = min(timeout, this->retransmit_limit);
+			}
+			if (this->retransmit_jitter)
+			{
+				max_jitter = (timeout / 100.0) * this->retransmit_jitter;
+				timeout -= max_jitter * (random() / (RAND_MAX + 1.0));
+			}
 			if (this->initiating.retransmitted)
 			{
 				DBG1(DBG_IKE, "retransmit %d of request with message ID %d",
@@ -2346,5 +2353,11 @@ task_manager_v2_t *task_manager_v2_create(ike_sa_t *ike_sa)
 					"%s.make_before_break", FALSE, lib->ns),
 	);
 
+	if (this->retransmit_base > 1)
+	{	/* based on 1000 * timeout * base^try */
+		this->retransmit_tries_max = log(UINT32_MAX/
+										 (1000.0 * this->retransmit_timeout))/
+									 log(this->retransmit_base);
+	}
 	return &this->public;
 }
diff --git a/src/libcharon/sa/task_manager.c b/src/libcharon/sa/task_manager.c
index e1c8d23b4..b3f589e0f 100644
--- a/src/libcharon/sa/task_manager.c
+++ b/src/libcharon/sa/task_manager.c
@@ -25,7 +25,7 @@
 u_int task_manager_total_retransmit_timeout()
 {
 	double timeout, base, limit = 0, total = 0;
-	int tries, i;
+	int tries, max_tries = 0, i;
 
 	tries = lib->settings->get_int(lib->settings, "%s.retransmit_tries",
 								   RETRANSMIT_TRIES, lib->ns);
@@ -36,9 +36,18 @@ u_int task_manager_total_retransmit_timeout()
 	limit = lib->settings->get_double(lib->settings, "%s.retransmit_limit",
 									  0, lib->ns);
 
+	if (base > 1)
+	{
+		max_tries = log(UINT32_MAX/(1000.0 * timeout))/log(base);
+	}
+
 	for (i = 0; i <= tries; i++)
 	{
-		double interval = timeout * pow(base, i);
+		double interval = UINT32_MAX/1000.0;
+		if (max_tries && i <= max_tries)
+		{
+			interval = timeout * pow(base, i);
+		}
 		if (limit)
 		{
 			interval = min(interval, limit);