diff --git lib/rubygems.rb lib/rubygems.rb
index cd7434ca87..f3671d9f2a 100644
--- lib/rubygems.rb
+++ lib/rubygems.rb
@@ -10,7 +10,7 @@
 require 'thread'
 
 module Gem
-  VERSION = "2.7.6.1"
+  VERSION = "2.7.6.2"
 end
 
 # Must be first since it unloads the prelude from 1.9.2
@@ -270,12 +270,7 @@ def self.find_spec_for_exe name, exec_name, requirements
 
     return loaded if loaded && dep.matches_spec?(loaded)
 
-    find_specs = proc { dep.matching_specs(true) }
-    if dep.to_s == "bundler (>= 0.a)"
-      specs = Gem::BundlerVersionFinder.without_filtering(&find_specs)
-    else
-      specs = find_specs.call
-    end
+    specs = dep.matching_specs(true)
 
     specs = specs.find_all { |spec|
       spec.executables.include? exec_name
diff --git lib/rubygems/bundler_version_finder.rb lib/rubygems/bundler_version_finder.rb
index baca170840..ba25399d1e 100644
--- lib/rubygems/bundler_version_finder.rb
+++ lib/rubygems/bundler_version_finder.rb
@@ -1,12 +1,4 @@
 module Gem::BundlerVersionFinder
-  @without_filtering = false
-
-  def self.without_filtering
-    without_filtering, @without_filtering = true, @without_filtering
-    yield
-  ensure
-    @without_filtering = without_filtering
-  end
 
   def self.bundler_version
     version, _ = bundler_version_with_reason
@@ -17,8 +9,6 @@ def self.bundler_version
   end
 
   def self.bundler_version_with_reason
-    return if @without_filtering
-
     if v = ENV["BUNDLER_VERSION"]
       return [v, "`$BUNDLER_VERSION`"]
     end
@@ -36,7 +26,7 @@ def self.missing_version_message
     return unless vr = bundler_version_with_reason
     <<-EOS
 Could not find 'bundler' (#{vr.first}) required by #{vr.last}.
-To update to the lastest version installed on your system, run `bundle update --bundler`.
+To update to the latest version installed on your system, run `bundle update --bundler`.
 To install the missing version, run `gem install bundler:#{vr.first}`
     EOS
   end
@@ -44,20 +34,14 @@ def self.missing_version_message
   def self.compatible?(spec)
     return true unless spec.name == "bundler".freeze
     return true unless bundler_version = self.bundler_version
-    if bundler_version.segments.first >= 2
-      spec.version == bundler_version
-    else # 1.x
-      spec.version.segments.first < 2
-    end
+
+    spec.version.segments.first == bundler_version.segments.first
   end
 
   def self.filter!(specs)
     return unless bundler_version = self.bundler_version
-    if bundler_version.segments.first >= 2
-      specs.reject! { |spec| spec.version != bundler_version }
-    else # 1.x
-      specs.reject! { |spec| spec.version.segments.first >= 2}
-    end
+
+    specs.reject! { |spec| spec.version.segments.first != bundler_version.segments.first }
   end
 
   def self.bundle_update_bundler_version
diff --git test/rubygems/test_gem.rb test/rubygems/test_gem.rb
index 693e5e0969..419497c75f 100644
--- test/rubygems/test_gem.rb
+++ test/rubygems/test_gem.rb
@@ -209,6 +209,41 @@ def test_activate_bin_path_resolves_eagerly
     assert_equal %w(a-1 b-2 c-1), loaded_spec_names
   end
 
+  def test_activate_bin_path_gives_proper_error_for_bundler
+    bundler = util_spec 'bundler', '2' do |s|
+      s.executables = ['bundle']
+    end
+
+    install_specs bundler
+
+    File.open("Gemfile.lock", "w") do |f|
+      f.write <<-L.gsub(/ {8}/, "")
+        GEM
+          remote: https://rubygems.org/
+          specs:
+
+        PLATFORMS
+          ruby
+
+        DEPENDENCIES
+
+        BUNDLED WITH
+          9999
+      L
+    end
+
+    File.open("Gemfile", "w") { |f| f.puts('source "https://rubygems.org"') }
+
+    e = assert_raises Gem::GemNotFoundException do
+      load Gem.activate_bin_path("bundler", "bundle", ">= 0.a")
+    end
+
+    assert_includes e.message, "Could not find 'bundler' (9999) required by your #{File.expand_path("Gemfile.lock")}."
+    assert_includes e.message, "To update to the latest version installed on your system, run `bundle update --bundler`."
+    assert_includes e.message, "To install the missing version, run `gem install bundler:9999`"
+    refute_includes e.message, "can't find gem bundler (>= 0.a) with executable bundle"
+  end
+
   def test_self_bin_path_no_exec_name
     e = assert_raises ArgumentError do
       Gem.bin_path 'a'
diff --git test/rubygems/test_gem_bundler_version_finder.rb test/rubygems/test_gem_bundler_version_finder.rb
index 7dafe13033..3b63b89423 100644
--- test/rubygems/test_gem_bundler_version_finder.rb
+++ test/rubygems/test_gem_bundler_version_finder.rb
@@ -88,20 +88,21 @@ def test_compatible
     bvf.stub(:bundler_version, v("2.1.1.1")) do
       assert bvf.compatible?(util_spec("foo"))
       assert bvf.compatible?(util_spec("bundler", "2.1.1.1"))
-      refute bvf.compatible?(util_spec("bundler", "2.1.1.a"))
+      assert bvf.compatible?(util_spec("bundler", "2.1.1.a"))
+      assert bvf.compatible?(util_spec("bundler", "2.999"))
       refute bvf.compatible?(util_spec("bundler", "1.999"))
-      refute bvf.compatible?(util_spec("bundler", "2.999"))
+      refute bvf.compatible?(util_spec("bundler", "3.0.0"))
     end
   end
 
   def test_filter
-    versions = %w[1 1.0 1.0.1.1 2.a 3 3.0]
+    versions = %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1]
     specs = versions.map { |v| util_spec("bundler", v) }
 
-    assert_equal %w[1 1.0 1.0.1.1 2.a 3 3.0], util_filter_specs(specs).map(&:version).map(&:to_s)
+    assert_equal %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
 
     bvf.stub(:bundler_version, v("2.1.1.1")) do
-      assert_empty util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[2 2.a 2.0 2.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
     end
     bvf.stub(:bundler_version, v("1.1.1.1")) do
       assert_equal %w[1 1.0 1.0.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
@@ -110,10 +111,10 @@ def test_filter
       assert_equal %w[1 1.0 1.0.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
     end
     bvf.stub(:bundler_version, v("2.a")) do
-      assert_equal %w[2.a], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[2 2.a 2.0 2.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
     end
     bvf.stub(:bundler_version, v("3")) do
-      assert_equal %w[3 3.0], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[3 3.a 3.0 3.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
     end
   end
 
diff --git test/rubygems/test_gem_dependency.rb test/rubygems/test_gem_dependency.rb
index d7eec3c090..3c11868671 100644
--- test/rubygems/test_gem_dependency.rb
+++ test/rubygems/test_gem_dependency.rb
@@ -358,7 +358,7 @@ def test_to_specs_respects_bundler_version
         dep.to_specs
       end
 
-      assert_match "Could not find 'bundler' (3.5) required by reason.\nTo update to the lastest version installed on your system, run `bundle update --bundler`.\nTo install the missing version, run `gem install bundler:3.5`\n", e.message
+      assert_match "Could not find 'bundler' (3.5) required by reason.\nTo update to the latest version installed on your system, run `bundle update --bundler`.\nTo install the missing version, run `gem install bundler:3.5`\n", e.message
     end
 
     Gem::BundlerVersionFinder.stub(:bundler_version_with_reason, ["2.0.0.pre.1", "reason"]) do