diff --git a/bundler/lib/dependabot/bundler/file_updater/requirement_replacer.rb b/bundler/lib/dependabot/bundler/file_updater/requirement_replacer.rb
index 8e9c8ca10a6..5cb05e05a82 100644
--- a/bundler/lib/dependabot/bundler/file_updater/requirement_replacer.rb
+++ b/bundler/lib/dependabot/bundler/file_updater/requirement_replacer.rb
@@ -167,6 +167,8 @@ def space_after_specifier?(requirement_nodes)
             req_string.include?(" ")
           end
 
+          EQUALITY_OPERATOR = /(?<![<>!])=/.freeze
+
           def use_equality_operator?(requirement_nodes)
             return true if requirement_nodes.none?
 
@@ -178,7 +180,7 @@ def use_equality_operator?(requirement_nodes)
                 requirement_nodes.first.children.first.loc.expression.source
               end
 
-            req_string.match?(/(?<![<>!])=/)
+            req_string.match?(EQUALITY_OPERATOR)
           end
 
           def new_requirement_string(quote_characters:,
@@ -203,7 +205,7 @@ def serialized_req(req, use_equality_operator)
             # Gem::Requirement serializes exact matches as a string starting
             # with `=`. We may need to remove that equality operator if it
             # wasn't used originally.
-            tmp_req = tmp_req.gsub(/(?<![<>!])=/, "") unless use_equality_operator
+            tmp_req = tmp_req.gsub(EQUALITY_OPERATOR, "") unless use_equality_operator
 
             tmp_req.strip
           end
diff --git a/bundler/spec/dependabot/bundler/update_checker/requirements_updater_spec.rb b/bundler/spec/dependabot/bundler/update_checker/requirements_updater_spec.rb
index d0ca3660cae..31599d1df3e 100644
--- a/bundler/spec/dependabot/bundler/update_checker/requirements_updater_spec.rb
+++ b/bundler/spec/dependabot/bundler/update_checker/requirements_updater_spec.rb
@@ -324,17 +324,25 @@
 
           context "and one is a != requirement" do
             context "that is binding" do
-              let(:gemspec_requirement_string) { "~> 1.4, != 1.8.0" }
+              let(:gemspec_requirement_string) { "~> 1.4, != #{latest_version}" }
               its([:requirement]) { is_expected.to eq("~> 1.4") }
             end
 
             context "that is not binding" do
-              let(:gemspec_requirement_string) { "~> 1.4.0, != 1.5.0" }
+              let(:gemspec_requirement_string) { "~> 1.4, != #{latest_resolvable_version}" }
               its([:requirement]) do
-                is_expected.to eq(">= 1.4, != 1.5.0, < 1.9")
+                is_expected.to eq("~> 1.4, != #{latest_resolvable_version}")
               end
             end
           end
+
+          context "when latest version is denied" do
+            let(:latest_version) { "2.0.4" }
+            let(:latest_resolvable_version) { "2.0.3" }
+            let(:gemspec_requirement_string) { ">= 2.0.0, != 2.0.4" }
+
+            its([:requirement]) { is_expected.to eq(">= 2.0.0, != 2.0.4") }
+          end
         end
 
         context "when a beta version was used in the old requirement" do
@@ -400,6 +408,20 @@
           context "when there are multiple requirements" do
             let(:gemspec_requirement_string) { "> 1.0.0, <= 1.4.0" }
             its([:requirement]) { is_expected.to eq("> 1.0.0, <= 1.9.0") }
+
+            context "and one is a != requirement" do
+              context "that is binding" do
+                let(:gemspec_requirement_string) { "~> 1.4, != #{latest_resolvable_version}" }
+                its([:requirement]) { is_expected.to eq("~> 1.4") }
+              end
+
+              context "that is not binding" do
+                let(:gemspec_requirement_string) { "~> 1.4, != #{latest_version}" }
+                its([:requirement]) do
+                  is_expected.to eq("~> 1.4, != #{latest_version}")
+                end
+              end
+            end
           end
 
           context "when a beta version was used in the old requirement" do