diff --git a/python/spec/dependabot/python/update_checker/pip_version_resolver_spec.rb b/python/spec/dependabot/python/update_checker/pip_version_resolver_spec.rb
index 04328186d34c..ce40865bd1d9 100644
--- a/python/spec/dependabot/python/update_checker/pip_version_resolver_spec.rb
+++ b/python/spec/dependabot/python/update_checker/pip_version_resolver_spec.rb
@@ -77,14 +77,24 @@
 
     context "with a .python-version file" do
       let(:dependency_files) { [requirements_file, python_version_file] }
-      let(:python_version_content) { "3.7.0\n" }
-
+      let(:python_version_content) { "3.11.0\n" }
       it { is_expected.to eq(Gem::Version.new("3.2.4")) }
 
-      context "that disallows the latest version" do
+      context "that is set to the oldest version of python supported by Dependabot" do
         let(:python_version_content) { "3.5.3\n" }
         it { is_expected.to eq(Gem::Version.new("2.2.24")) }
       end
+
+      context "that is set to a python version no longer supported by Dependabot" do
+        let(:python_version_content) { "3.4.0\n" }
+        it "raises a helpful error" do
+          expect { subject }.to raise_error(Dependabot::DependencyFileNotResolvable) do |err|
+            expect(err.message).to start_with(
+              "Dependabot detected the following Python requirement for your project: '3.4.0'."
+            )
+          end
+        end
+      end
     end
   end
 
@@ -111,23 +121,25 @@
 
     context "with a .python-version file" do
       let(:dependency_files) { [requirements_file, python_version_file] }
-      let(:python_version_content) { "3.7.0\n" }
+      let(:python_version_content) { "3.11.0\n" }
 
       it { is_expected.to eq(Gem::Version.new("2.1.1")) }
 
-      context "that disallows all fixed versions" do
+      context "that is set to the oldest version of python supported by Dependabot" do
         let(:python_version_content) { "3.5.3\n" }
-        let(:dependency_version) { "3.0.0" }
-        let(:dependency_requirements) do
-          [{
-            file: "requirements.txt",
-            requirement: "==3.0.0",
-            groups: [],
-            source: nil
-          }]
-        end
+        it { is_expected.to eq(Gem::Version.new("2.1.1")) }
+      end
 
-        it { is_expected.to be_nil }
+      context "that is set to a python version no longer supported by Dependabot" do
+        let(:python_version_content) { "3.4.0\n" }
+
+        it "raises a helpful error" do
+          expect { subject }.to raise_error(Dependabot::DependencyFileNotResolvable) do |err|
+            expect(err.message).to start_with(
+              "Dependabot detected the following Python requirement for your project: '3.4.0'."
+            )
+          end
+        end
       end
     end
   end
diff --git a/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb b/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb
index 0f0f9f6d2fd8..18c39f1c1d21 100644
--- a/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb
+++ b/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb
@@ -208,20 +208,15 @@
         end
       end
 
-      context "that is unsupported" do
+      context "that is set to a python version no longer supported by Dependabot" do
         let(:pipfile_fixture_name) { "required_python_unsupported" }
 
         it "raises a helpful error" do
-          expect { subject }.
-            to raise_error(Dependabot::DependencyFileNotResolvable) do |error|
-              expect(error.message).
-                to start_with("Dependabot detected the following Python")
-              expect(error.message).to include("3.4.*")
-              expect(error.message).
-                to include(
-                  "supported in Dependabot: 3.11.4, 3.11.3, 3.11.2, 3.11.1, 3.11.0, 3.10.12, 3.10.11, 3.10.10, 3.10.9"
-                )
-            end
+          expect { subject }.to raise_error(Dependabot::DependencyFileNotResolvable) do |err|
+            expect(err.message).to start_with(
+              "Dependabot detected the following Python requirement for your project: '3.4.*'."
+            )
+          end
         end
       end
 
diff --git a/python/spec/dependabot/python/update_checker_spec.rb b/python/spec/dependabot/python/update_checker_spec.rb
index 312b63312156..e7138baca599 100644
--- a/python/spec/dependabot/python/update_checker_spec.rb
+++ b/python/spec/dependabot/python/update_checker_spec.rb
@@ -225,9 +225,8 @@
 
         context "that is set to a python version no longer supported by Dependabot" do
           let(:python_version_content) { "3.4.0\n" }
-          it "raises a Dependabot::DependencyFileNotResolvable error" do
-            expect { checker.latest_resolvable_version }.
-              to raise_error(Dependabot::DependencyFileNotResolvable) do |err|
+          it "raises a helpful error" do
+            expect { subject }.to raise_error(Dependabot::DependencyFileNotResolvable) do |err|
               expect(err.message).to start_with(
                 "Dependabot detected the following Python requirement for your project: '3.4.0'."
               )