diff --git a/lib/bundler/injector.rb b/lib/bundler/injector.rb
index cb644a7f69..a738992068 100644
--- a/lib/bundler/injector.rb
+++ b/lib/bundler/injector.rb
@@ -86,7 +86,7 @@ module Bundler
       segments = version.segments
       seg_end_index = version >= Gem::Version.new("1.0") ? 1 : 2
 
-      prerelease_suffix = version.to_s.gsub(version.release.to_s, "") if version.prerelease?
+      prerelease_suffix = version.to_s.delete_prefix(version.release.to_s) if version.prerelease?
       "#{version_prefix}#{segments[0..seg_end_index].join(".")}#{prerelease_suffix}"
     end
 
diff --git a/spec/bundler/commands/add_spec.rb b/spec/bundler/commands/add_spec.rb
index 1eaff913c3..9398bfb3d1 100644
--- a/spec/bundler/commands/add_spec.rb
+++ b/spec/bundler/commands/add_spec.rb
@@ -9,6 +9,7 @@ RSpec.describe "bundle add" do
       build_gem "bar", "0.12.3"
       build_gem "cat", "0.12.3.pre"
       build_gem "dog", "1.1.3.pre"
+      build_gem "lemur", "3.1.1.pre.2023.1.1"
     end
 
     build_git "foo", "2.0"
@@ -51,6 +52,13 @@ RSpec.describe "bundle add" do
       expect(bundled_app_gemfile.read).to match(/gem "dog", "~> 1.1.pre"/)
       expect(the_bundle).to include_gems "dog 1.1.3.pre"
     end
+
+    it "version requirement becomes ~> major.minor.pre.tail when resolved version has a very long tail pre version" do
+      bundle "add 'lemur'"
+      # the trailing pre purposely matches the release version to ensure that subbing the release doesn't change the pre.version"
+      expect(bundled_app_gemfile.read).to match(/gem "lemur", "~> 3.1.pre.2023.1.1"/)
+      expect(the_bundle).to include_gems "lemur 3.1.1.pre.2023.1.1"
+    end
   end
 
   describe "with --version" do