diff --git a/test/README b/test/README
index 11eaf18f..10f127cb 100644
--- a/test/README
+++ b/test/README
@@ -25,6 +25,7 @@ that you know if you break anything.
   - gdb(1)
   - gpg(1)
   - python(1)
+  - xapian-metadata(1)
 
 If your system lacks these tools or have older, non-upgradable versions
 of these, please (possibly compile and) install these to some other
diff --git a/test/T530-upgrade.sh b/test/T530-upgrade.sh
new file mode 100755
index 00000000..c599dacf
--- /dev/null
+++ b/test/T530-upgrade.sh
@@ -0,0 +1,57 @@
+#!/usr/bin/env bash
+test_description='database upgrades'
+. $(dirname "$0")/test-lib.sh || exit 1
+
+test_require_external_prereq xapian-metadata
+
+XAPIAN_PATH=$MAIL_DIR/.notmuch/xapian
+BACKUP_PATH=$MAIL_DIR/.notmuch
+
+delete_feature () {
+    local key=$1
+    features=$(xapian-metadata get $XAPIAN_PATH features | grep -v "^$key")
+    xapian-metadata set $XAPIAN_PATH features "$features"
+}
+
+add_email_corpus
+
+for key in 'multiple paths per message' \
+	       'relative directory paths' \
+	       'exact folder:/path: search' \
+	       'mail documents for missing messages' \
+	       'modification tracking'; do
+    backup_database
+    test_begin_subtest "upgrade is triggered by missing '$key'"
+    delete_feature "$key"
+    output=$(notmuch new | grep Welcome)
+    test_expect_equal \
+	"$output" \
+	"Welcome to a new version of notmuch! Your database will now be upgraded."
+
+    restore_database
+
+    backup_database
+    test_begin_subtest "backup can be restored ['$key']"
+    notmuch dump > BEFORE
+    delete_feature "$key"
+    notmuch new
+    notmuch tag -inbox '*'
+    dump_file=$(echo ${BACKUP_PATH}/dump*)
+    notmuch restore --input=$dump_file
+    notmuch dump > AFTER
+    test_expect_equal_file BEFORE AFTER
+    restore_database
+done
+
+for key in 'from/subject/message-ID in database' \
+	       'indexed MIME types' \
+	       'index body and headers separately'; do
+    backup_database
+    test_begin_subtest "upgrade not triggered by missing '$key'"
+    delete_feature "$key"
+    output=$(notmuch new | grep Welcome)
+    test_expect_equal "$output" ""
+    restore_database
+done
+
+test_done
diff --git a/test/test-lib.sh b/test/test-lib.sh
index c23a0d20..29baa0c1 100644
--- a/test/test-lib.sh
+++ b/test/test-lib.sh
@@ -1270,3 +1270,4 @@ test_declare_external_prereq gpg
 test_declare_external_prereq openssl
 test_declare_external_prereq gpgsm
 test_declare_external_prereq ${NOTMUCH_PYTHON}
+test_declare_external_prereq xapian-metadata