diff --git a/lib/bundler/retry.rb b/lib/bundler/retry.rb
index b95c42c361..090cb7e2ca 100644
--- a/lib/bundler/retry.rb
+++ b/lib/bundler/retry.rb
@@ -50,7 +50,7 @@ module Bundler
       end
       return true unless name
       Bundler.ui.info "" unless Bundler.ui.debug? # Add new line in case dots preceded this
-      Bundler.ui.warn "Retrying #{name} due to error (#{current_run.next}/#{total_runs}): #{e.class} #{e.message}", Bundler.ui.debug?
+      Bundler.ui.warn "Retrying #{name} due to error (#{current_run.next}/#{total_runs}): #{e.class} #{e.message}", true
     end
 
     def keep_trying?
diff --git a/lib/bundler/ui/shell.rb b/lib/bundler/ui/shell.rb
index 899f3dcb87..16e7cc70b5 100644
--- a/lib/bundler/ui/shell.rb
+++ b/lib/bundler/ui/shell.rb
@@ -130,7 +130,7 @@ module Bundler
       def tell_err(message, color = nil, newline = nil)
         return if @shell.send(:stderr).closed?
 
-        newline ||= !message.to_s.match?(/( |\t)\Z/)
+        newline = !message.to_s.match?(/( |\t)\Z/) if newline.nil?
         message = word_wrap(message) if newline.is_a?(Hash) && newline[:wrap]
 
         color = nil if color && !$stderr.tty?
diff --git a/spec/bundler/bundler/retry_spec.rb b/spec/bundler/bundler/retry_spec.rb
index b893580d72..ffbc078074 100644
--- a/spec/bundler/bundler/retry_spec.rb
+++ b/spec/bundler/bundler/retry_spec.rb
@@ -68,7 +68,7 @@ RSpec.describe Bundler::Retry do
       it "print error message with newlines" do
         allow(Bundler.ui).to  receive(:debug?).and_return(false)
         expect(Bundler.ui).to receive(:info).with("").twice
-        expect(Bundler.ui).to receive(:warn).with(failure_message, false)
+        expect(Bundler.ui).to receive(:warn).with(failure_message, true)
 
         expect do
           Bundler::Retry.new("test", [], 1).attempt do
diff --git a/spec/bundler/bundler/ui/shell_spec.rb b/spec/bundler/bundler/ui/shell_spec.rb
index 15120a8a41..e1340e5923 100644
--- a/spec/bundler/bundler/ui/shell_spec.rb
+++ b/spec/bundler/bundler/ui/shell_spec.rb
@@ -21,9 +21,12 @@ RSpec.describe Bundler::UI::Shell do
 
   describe "#warn" do
     before { subject.level = "warn" }
-    it "prints to stderr" do
+    it "prints to stderr, implicitly adding a newline" do
       expect { subject.warn("warning") }.to output("warning\n").to_stderr
     end
+    it "can be told not to emit a newline" do
+      expect { subject.warn("warning", false) }.to output("warning").to_stderr
+    end
   end
 
   describe "#debug" do