diff --git a/databases/ruby-sqlite3/Makefile b/databases/ruby-sqlite3/Makefile
index 332bd1c26bb..d0cfef3a4bd 100644
--- a/databases/ruby-sqlite3/Makefile
+++ b/databases/ruby-sqlite3/Makefile
@@ -1,9 +1,8 @@
-# $OpenBSD: Makefile,v 1.41 2018/06/13 22:26:52 jeremy Exp $
+# $OpenBSD: Makefile,v 1.42 2019/03/28 04:33:30 jeremy Exp $
 
 COMMENT=	access a SQLite3 database from ruby
 
-DISTNAME=	sqlite3-1.3.13
-REVISION=	1
+DISTNAME=	sqlite3-1.4.0
 CATEGORIES=	databases
 
 MAINTAINER =	Jeremy Evans <jeremy@openbsd.org>
@@ -25,7 +24,7 @@ TEST_DEPENDS=	devel/ruby-mocha,${MODRUBY_FLAVOR} \
 			${FULLPKGNAME}:${BUILD_PKGPATH}
 
 do-test:
-	cd ${WRKSRC}/test && ${RUBY} -I . -rubygems -e \
+	cd ${WRKSRC}/test && ${RUBY} -I . -e \
 		"require 'sqlite3'; Dir['test_*.rb'].each{|f| load(f)}"
 
 .include <bsd.port.mk>
diff --git a/databases/ruby-sqlite3/distinfo b/databases/ruby-sqlite3/distinfo
index c2547fb289d..ac460674254 100644
--- a/databases/ruby-sqlite3/distinfo
+++ b/databases/ruby-sqlite3/distinfo
@@ -1,2 +1,2 @@
-SHA256 (sqlite3-1.3.13.gem) = sTiiLg27tpvghUBnHav2AlmUN+OJpUBUuxd/btH9LgY=
-SIZE (sqlite3-1.3.13.gem) = 64512
+SHA256 (sqlite3-1.4.0.gem) = 3Y0pkcesrfecAKseF14QXHOJvJTzzEyKrhc9LTq+r14=
+SIZE (sqlite3-1.4.0.gem) = 70144
diff --git a/databases/ruby-sqlite3/patches/patch-ext_sqlite3_database_h b/databases/ruby-sqlite3/patches/patch-ext_sqlite3_database_h
deleted file mode 100644
index 942a9ac93e4..00000000000
--- a/databases/ruby-sqlite3/patches/patch-ext_sqlite3_database_h
+++ /dev/null
@@ -1,15 +0,0 @@
-$OpenBSD: patch-ext_sqlite3_database_h,v 1.1 2012/06/29 16:40:31 jeremy Exp $
-
-Define a dummy RB_GC_GUARD so it works on rubinius 1.2.4.
-
---- ext/sqlite3/database.h.orig	Tue Jun 26 11:21:00 2012
-+++ ext/sqlite3/database.h	Tue Jun 26 11:21:44 2012
-@@ -12,4 +12,8 @@ typedef sqlite3Ruby * sqlite3RubyPtr;
- 
- void init_sqlite3_database();
- 
-+#ifndef RB_GC_GUARD
-+#define RB_GC_GUARD(x) x
-+#endif
-+
- #endif
diff --git a/databases/ruby-sqlite3/patches/patch-test_test_integration_pending_rb b/databases/ruby-sqlite3/patches/patch-test_test_integration_pending_rb
deleted file mode 100644
index 99f94c55cf2..00000000000
--- a/databases/ruby-sqlite3/patches/patch-test_test_integration_pending_rb
+++ /dev/null
@@ -1,15 +0,0 @@
-$OpenBSD: patch-test_test_integration_pending_rb,v 1.2 2012/06/29 16:40:31 jeremy Exp $
-
-Fix hang when running the test suite using rubinius.  skip would be
-better but rubinius uses ruby 1.8 stdlib and doesn't support it.
-
---- test/test_integration_pending.rb.orig	Wed Dec 31 16:00:00 1969
-+++ test/test_integration_pending.rb	Tue Jun 26 10:44:55 2012
-@@ -21,6 +21,7 @@ class TC_Integration_Pending < SQLite3::TestCase
- 
-   def test_busy_handler_outwait
-     skip("not working in 1.9") if RUBY_VERSION >= '1.9'
-+    return if defined?(RUBY_ENGINE) && RUBY_ENGINE == 'rbx'
- 
-     busy = Mutex.new
-     busy.lock
diff --git a/databases/ruby-sqlite3/pkg/PLIST b/databases/ruby-sqlite3/pkg/PLIST
index e69cbb57c04..efca94f5dac 100644
--- a/databases/ruby-sqlite3/pkg/PLIST
+++ b/databases/ruby-sqlite3/pkg/PLIST
@@ -1,6 +1,8 @@
-@comment $OpenBSD: PLIST,v 1.13 2016/11/04 21:30:37 jeremy Exp $
+@comment $OpenBSD: PLIST,v 1.14 2019/03/28 04:33:31 jeremy Exp $
 ${GEM_LIB}/cache/${DISTNAME}.gem
 ${GEM_LIB}/gems/${DISTNAME}/
+${GEM_LIB}/gems/${DISTNAME}/.gemtest
+${GEM_LIB}/gems/${DISTNAME}/.travis.yml
 ${GEM_LIB}/gems/${DISTNAME}/API_CHANGES.rdoc
 ${GEM_LIB}/gems/${DISTNAME}/CHANGELOG.rdoc
 ${GEM_LIB}/gems/${DISTNAME}/ChangeLog.cvs
@@ -9,6 +11,7 @@ ${GEM_LIB}/gems/${DISTNAME}/LICENSE
 ${GEM_LIB}/gems/${DISTNAME}/Manifest.txt
 ${GEM_LIB}/gems/${DISTNAME}/README.rdoc
 ${GEM_LIB}/gems/${DISTNAME}/Rakefile
+${GEM_LIB}/gems/${DISTNAME}/appveyor.yml
 ${GEM_LIB}/gems/${DISTNAME}/faq/
 ${GEM_LIB}/gems/${DISTNAME}/faq/faq.rb
 ${GEM_LIB}/gems/${DISTNAME}/faq/faq.yml
@@ -25,21 +28,24 @@ ${GEM_LIB}/gems/${DISTNAME}/lib/sqlite3/statement.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/sqlite3/translator.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/sqlite3/value.rb
 ${GEM_LIB}/gems/${DISTNAME}/lib/sqlite3/version.rb
+${GEM_LIB}/gems/${DISTNAME}/rakelib/
+${GEM_LIB}/gems/${DISTNAME}/rakelib/faq.rake
+${GEM_LIB}/gems/${DISTNAME}/rakelib/gem.rake
+${GEM_LIB}/gems/${DISTNAME}/rakelib/native.rake
+${GEM_LIB}/gems/${DISTNAME}/rakelib/vendor_sqlite3.rake
 ${GEM_LIB}/gems/${DISTNAME}/setup.rb
-${GEM_LIB}/gems/${DISTNAME}/tasks/
-${GEM_LIB}/gems/${DISTNAME}/tasks/faq.rake
-${GEM_LIB}/gems/${DISTNAME}/tasks/gem.rake
-${GEM_LIB}/gems/${DISTNAME}/tasks/native.rake
-${GEM_LIB}/gems/${DISTNAME}/tasks/vendor_sqlite3.rake
 ${GEM_LIB}/gems/${DISTNAME}/test/
 ${GEM_LIB}/gems/${DISTNAME}/test/helper.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_backup.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_collation.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_database.rb
+${GEM_LIB}/gems/${DISTNAME}/test/test_database_flags.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_database_readonly.rb
+${GEM_LIB}/gems/${DISTNAME}/test/test_database_readwrite.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_deprecated.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_encoding.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_integration.rb
+${GEM_LIB}/gems/${DISTNAME}/test/test_integration_aggregate.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_integration_open_close.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_integration_pending.rb
 ${GEM_LIB}/gems/${DISTNAME}/test/test_integration_resultset.rb