diff --git a/src/conns.c b/src/conns.c
index 19aaa49c..b70fbdeb 100644
--- a/src/conns.c
+++ b/src/conns.c
@@ -28,6 +28,7 @@
 #include "conns.h"
 #include "heap.h"
 #include "log.h"
+#include "sock.h"
 #include "stats.h"
 
 void conn_struct_init(struct conn_s *connptr) {
@@ -82,14 +83,10 @@ void conn_destroy_contents (struct conn_s *connptr)
         assert (connptr != NULL);
 
         if (connptr->client_fd != -1)
-                if (close (connptr->client_fd) < 0)
-                        log_message (LOG_INFO, "Client (%d) close message: %s",
-                                     connptr->client_fd, strerror (errno));
+                close_socket (connptr->client_fd);
         connptr->client_fd = -1;
         if (connptr->server_fd != -1)
-                if (close (connptr->server_fd) < 0)
-                        log_message (LOG_INFO, "Server (%d) close message: %s",
-                                     connptr->server_fd, strerror (errno));
+                close_socket (connptr->server_fd);
         connptr->server_fd = -1;
 
         if (connptr->cbuffer)
diff --git a/src/reqs.c b/src/reqs.c
index 94ce7673..e3e7e311 100644
--- a/src/reqs.c
+++ b/src/reqs.c
@@ -1281,6 +1281,7 @@ static void relay_connection (struct conn_s *connptr)
                 if (write_buffer (connptr->server_fd, connptr->cbuffer) < 0)
                         break;
         }
+        shutdown (connptr->server_fd, SHUT_WR);
 
         return;
 }
diff --git a/src/sock.c b/src/sock.c
index b3b0920d..50385506 100644
--- a/src/sock.c
+++ b/src/sock.c
@@ -212,6 +212,43 @@ int opensock (const char *host, int port, const char *bind_to)
         return sockfd;
 }
 
+/*
+ * Gracefully close a socket by completing the TCP close handshake.
+ * Send FIN via shutdown(SHUT_WR), then drain remaining data until
+ * the remote FIN arrives (read returns 0).  This keeps the fd open
+ * until both sides have exchanged FINs, preventing the socket from
+ * being orphaned in FIN_WAIT_2.
+ *
+ * Without this, close() orphans the socket while still in FIN_WAIT_2.
+ * Linux reaps orphaned FIN_WAIT_2 via net.ipv4.tcp_fin_timeout, but
+ * OpenBSD has no equivalent, so they persist indefinitely.
+ */
+void close_socket (int fd)
+{
+        char drain[4096];
+        ssize_t n;
+        struct timeval tv;
+
+        shutdown (fd, SHUT_WR);
+
+        tv.tv_sec = 10;
+        tv.tv_usec = 0;
+        setsockopt (fd, SOL_SOCKET, SO_RCVTIMEO, &tv, sizeof (tv));
+
+        for (;;) {
+                n = read (fd, drain, sizeof (drain));
+                if (n > 0)
+                        continue;
+                if (n == 0)
+                        break;
+                if (errno == EINTR)
+                        continue;
+                break;
+        }
+
+        close (fd);
+}
+
 /*
  * Set the socket to non blocking -rjkaes
  */
diff --git a/src/sock.h b/src/sock.h
index 70c44739..700e958e 100644
--- a/src/sock.h
+++ b/src/sock.h
@@ -53,6 +53,7 @@ union sockaddr_union {
 extern int opensock (const char *host, int port, const char *bind_to);
 extern int listen_sock (const char *addr, uint16_t port, sblist* listen_fds);
 
+extern void close_socket (int fd);
 extern int socket_nonblocking (int sock);
 extern int socket_blocking (int sock);