diff --git a/src/address.c b/src/address.c
index 9a544a5b..a2ac36f5 100644
--- a/src/address.c
+++ b/src/address.c
@@ -34,6 +34,7 @@
 #include <arpa/inet.h> /* inet_pton */
 #include <sys/un.h>
 #include <assert.h>
+#include <string.h>
 #include "address.h"
 
 
@@ -259,6 +260,30 @@ address_compare(const struct Address *addr_1, const struct Address *addr_2) {
     return result;
 }
 
+int
+address_addr_eq(const struct Address *addr, const struct sockaddr *sa) {
+    if (addr->type != SOCKADDR)
+        return 0;
+
+    if (address_sa(addr)->sa_family != sa->sa_family)
+        return 0;
+
+    switch (address_sa(addr)->sa_family) {
+        case AF_INET:
+            return !memcmp(&((struct sockaddr_in *)addr->data)->sin_addr,
+                    &((struct sockaddr_in *)sa)->sin_addr,
+                    sizeof(((struct sockaddr_in *)sa)->sin_addr));
+
+        case AF_INET6:
+            return !memcmp(&((struct sockaddr_in6 *)addr->data)->sin6_addr,
+                    &((struct sockaddr_in6 *)sa)->sin6_addr,
+                    sizeof(((struct sockaddr_in6 *)sa)->sin6_addr));
+
+        default:
+            return 0;
+    }
+}
+
 int
 address_is_hostname(const struct Address *addr) {
     return addr != NULL && addr->type == HOSTNAME;
diff --git a/src/address.h b/src/address.h
index 66125eb6..6d0f5f2f 100644
--- a/src/address.h
+++ b/src/address.h
@@ -44,6 +44,7 @@ struct Address *new_address_sa(const struct sockaddr *, socklen_t);
 struct Address *copy_address(const struct Address *);
 size_t address_len(const struct Address *);
 int address_compare(const struct Address *, const struct Address *);
+int address_addr_eq(const struct Address *, const struct sockaddr *);
 int address_is_hostname(const struct Address *);
 int address_is_sockaddr(const struct Address *);
 int address_is_wildcard(const struct Address *);
diff --git a/src/connection.c b/src/connection.c
index c10a1090..1e3e7495 100644
--- a/src/connection.c
+++ b/src/connection.c
@@ -630,23 +630,45 @@ initiate_server_connect(struct Connection *con, struct ev_loop *loop) {
 
     if (con->listener->transparent_proxy &&
             con->client.addr.ss_family == con->server.addr.ss_family) {
+        int result;
+
+        if (address_addr_eq(con->listener->address,
+                    (struct sockaddr *)&con->client.addr)) {
+            /* Client is the same host as the listener, bind to a new port. */
+            struct sockaddr_storage self = con->client.addr;
+
+            switch (con->client.addr.ss_family) {
+                case AF_INET:
+                    ((struct sockaddr_in *)&self)->sin_port = 0;
+                    break;
+
+                case AF_INET6:
+                    ((struct sockaddr_in6 *)&self)->sin6_port = 0;
+                    break;
+            }
+
+            result = bind(sockfd, (struct sockaddr *)&self,
+                    con->client.addr_len);
+        } else {
 #ifdef IP_TRANSPARENT
-        int on = 1;
-        int result = setsockopt(sockfd, SOL_IP, IP_TRANSPARENT, &on, sizeof(on));
+            int on = 1;
+            result = setsockopt(sockfd, SOL_IP, IP_TRANSPARENT, &on, sizeof(on));
 #else
-        int result = -EPERM;
-        /* XXX error: not implemented would be better, but this shouldn't be
-         * reached since it is prohibited in the configuration parser. */
+            result = -EPERM;
+            /* XXX error: not implemented would be better, but this shouldn't be
+             * reached since it is prohibited in the configuration parser. */
 #endif
-        if (result < 0) {
-            err("setsockopt IP_TRANSPARENT failed: %s", strerror(errno));
-            close(sockfd);
-            abort_connection(con);
-            return;
+            if (result < 0) {
+                err("setsockopt IP_TRANSPARENT failed: %s", strerror(errno));
+                close(sockfd);
+                abort_connection(con);
+                return;
+            }
+
+            result = bind(sockfd, (struct sockaddr *)&con->client.addr,
+                    con->client.addr_len);
         }
 
-        result = bind(sockfd, (struct sockaddr *)&con->client.addr,
-                con->client.addr_len);
         if (result < 0) {
             err("bind failed: %s", strerror(errno));
             close(sockfd);