diff --git a/.travis.yml b/.travis.yml
index 57dec9ae49b..f34ea4ca811 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -47,6 +47,21 @@ matrix:
     # 3.x mode
     - rvm: 2.5.3
       env: RGV=v3.0.1 BUNDLER_SPEC_SUB_VERSION=3.0.0
+    # Ruby 2.5, Rubygems 2.7 and up
+    - rvm: 2.5.3
+      env: RGV=v2.7.7
+    # Ruby 2.4, Rubygems 2.6 and up
+    - rvm: 2.4.5
+      env: RGV=v2.6.14
+    - rvm: 2.4.5
+      env: RGV=v2.7.7
+    # Ruby 2.3, Rubygems 2.5 and up
+    - rvm: 2.3.7
+      env: RGV=v2.5.2
+    - rvm: 2.3.7
+      env: RGV=v2.6.14
+    - rvm: 2.3.7
+      env: RGV=v2.7.7
     # Ruby-head (we want to know how we're doing, but not fail the build)
     - rvm: ruby-head
       env: RGV=master
diff --git a/bundler.gemspec b/bundler.gemspec
index af65811f23d..fff5d0dfd57 100644
--- a/bundler.gemspec
+++ b/bundler.gemspec
@@ -34,7 +34,7 @@ Gem::Specification.new do |s|
 
   if s.version >= Gem::Version.new("2.a".dup)
     s.required_ruby_version     = ">= 2.3.0"
-    s.required_rubygems_version = ">= 3.0.0"
+    s.required_rubygems_version = ">= 2.5.0"
   else
     s.required_ruby_version     = ">= 1.8.7"
     s.required_rubygems_version = ">= 1.3.6"