diff --git a/contrib/ruby/ext/trilogy-ruby/cext.c b/contrib/ruby/ext/trilogy-ruby/cext.c
index 3a8bddcd..ea350fdc 100644
--- a/contrib/ruby/ext/trilogy-ruby/cext.c
+++ b/contrib/ruby/ext/trilogy-ruby/cext.c
@@ -43,9 +43,7 @@ static void mark_trilogy(void *ptr)
 static void free_trilogy(void *ptr)
 {
     struct trilogy_ctx *ctx = ptr;
-    if (ctx->conn.socket != NULL) {
-        trilogy_free(&ctx->conn);
-    }
+    trilogy_free(&ctx->conn);
     xfree(ptr);
 }
 
@@ -309,6 +307,7 @@ static int try_connect(struct trilogy_ctx *ctx, trilogy_handshake_t *handshake,
     int rc = args.rc;
 
     if (rc != TRILOGY_OK) {
+        trilogy_sock_close(sock);
         return rc;
     }
 
@@ -316,8 +315,10 @@ static int try_connect(struct trilogy_ctx *ctx, trilogy_handshake_t *handshake,
 escape the GVL on each wait operation without going through call_without_gvl */
     sock->wait_cb = _cb_ruby_wait;
     rc = trilogy_connect_send_socket(&ctx->conn, sock);
-    if (rc < 0)
+    if (rc < 0) {
+        trilogy_sock_close(sock);
         return rc;
+    }
 
     while (1) {
         rc = trilogy_connect_recv(&ctx->conn, handshake);
diff --git a/contrib/ruby/ext/trilogy-ruby/extconf.rb b/contrib/ruby/ext/trilogy-ruby/extconf.rb
index 05ad2aec..f618ef21 100644
--- a/contrib/ruby/ext/trilogy-ruby/extconf.rb
+++ b/contrib/ruby/ext/trilogy-ruby/extconf.rb
@@ -2,8 +2,12 @@
 
 # concatenate trilogy library sources to allow the compiler to optimise across
 # source files
+
+trilogy_src_dir = File.realpath("src", __dir__)
 File.binwrite("trilogy.c",
-  Dir["#{__dir__}/src/**/*.c"].map { |src| File.binread(src) }.join)
+  Dir["#{trilogy_src_dir}/**/*.c"].map { |src|
+    %{#line 1 "#{src}"\n} + File.binread(src)
+  }.join)
 
 $objs = %w[trilogy.o cast.o cext.o]
 $CFLAGS << " -I #{__dir__}/inc -std=gnu99 -fvisibility=hidden"
diff --git a/src/buffer.c b/src/buffer.c
index cdb95216..a4c78393 100644
--- a/src/buffer.c
+++ b/src/buffer.c
@@ -57,4 +57,9 @@ int trilogy_buffer_putc(trilogy_buffer_t *buffer, uint8_t c)
     return TRILOGY_OK;
 }
 
-void trilogy_buffer_free(trilogy_buffer_t *buffer) { free(buffer->buff); }
+void trilogy_buffer_free(trilogy_buffer_t *buffer)
+{
+    free(buffer->buff);
+    buffer->buff = NULL;
+    buffer->len = buffer->cap = 0;
+}