diff --git a/Gemfile b/Gemfile
index ec023deb..7a53659a 100644
--- a/Gemfile
+++ b/Gemfile
@@ -13,7 +13,7 @@ group :test do
   gem 'simplecov', '>= 0.9'
   gem 'timecop'
   gem 'tins'
-  gem 'webmock', '>= 1.10.1'
+  gem 'webmock', '>= 3.1.0'
 end
 
 gemspec
diff --git a/spec/cli_spec.rb b/spec/cli_spec.rb
index 5646f6cc..b7334cc2 100644
--- a/spec/cli_spec.rb
+++ b/spec/cli_spec.rb
@@ -2550,7 +2550,7 @@
     context 'with file' do
       before do
         @cli.options = @cli.options.merge('file' => fixture_path + '/long.png')
-        stub_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')
+        stub_request(:post, 'https://upload.twitter.com/1.1/media/upload.json').to_return(body: fixture('media.json'), headers: {content_type: 'application/json; charset=utf-8'})
         stub_post('/1.1/statuses/update.json').to_return(body: fixture('status.json'), headers: {content_type: 'application/json; charset=utf-8'})
       end
       it 'requests the correct resource' do
@@ -3892,13 +3892,13 @@
     context 'with file' do
       before do
         @cli.options = @cli.options.merge('file' => fixture_path + '/long.png')
-        stub_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')
+        stub_request(:post, 'https://upload.twitter.com/1.1/media/upload.json').to_return(body: fixture('media.json'), headers: {content_type: 'application/json; charset=utf-8'})
         stub_post('/1.1/statuses/update.json').to_return(body: fixture('status.json'), headers: {content_type: 'application/json; charset=utf-8'})
       end
       it 'requests the correct resource' do
         @cli.update('Testing')
         expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made
-        expect(a_post('/1.1/statuses/update_with_media.json')).to have_been_made
+        expect(a_post('/1.1/statuses/update.json')).to have_been_made
       end
       it 'has the correct output' do
         @cli.update('Testing')
diff --git a/spec/fixtures/media.json b/spec/fixtures/media.json
new file mode 100644
index 00000000..28fc2e43
--- /dev/null
+++ b/spec/fixtures/media.json
@@ -0,0 +1 @@
+{"image":{"w":428,"h":428,"image_type":"image/png"},"media_id":470030289822314497,"media_id_string":"470030289822314497","size":68900}
diff --git a/t.gemspec b/t.gemspec
index 934aaac5..398643b7 100644
--- a/t.gemspec
+++ b/t.gemspec
@@ -10,8 +10,8 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'oauth', '~> 0.5.1'
   spec.add_dependency 'retryable', '~> 2.0'
   spec.add_dependency 'thor', ['>= 0.19.1', '< 2']
-  spec.add_dependency 'twitter', '~> 6.0'
-  spec.add_development_dependency 'bundler', '~> 1.0'
+  spec.add_dependency 'twitter', '~> 6.2'
+  spec.add_development_dependency 'bundler', '~> 2.1'
   spec.author = 'Erik Michaels-Ober'
   spec.description = 'A command-line power tool for Twitter.'
   spec.email = 'sferik@gmail.com'