diff --git a/lib/bundler/self_manager.rb b/lib/bundler/self_manager.rb
index 024884cf2d..53eb2c1859 100644
--- a/lib/bundler/self_manager.rb
+++ b/lib/bundler/self_manager.rb
@@ -142,6 +142,7 @@ module Bundler
     end
 
     def find_latest_matching_spec(requirement)
+      Bundler.configure
       local_result = find_latest_matching_spec_from_collection(local_specs, requirement)
       return local_result if local_result && requirement.specific?
 
diff --git a/spec/bundler/commands/update_spec.rb b/spec/bundler/commands/update_spec.rb
index 160a09ed79..faf9db32d4 100644
--- a/spec/bundler/commands/update_spec.rb
+++ b/spec/bundler/commands/update_spec.rb
@@ -1685,7 +1685,7 @@ RSpec.describe "bundle update --bundler" do
   end
 
   it "allows updating to development versions if already installed locally" do
-    system_gems "bundler-9.0.0.dev"
+    system_gems "bundler-9.9.9"
 
     build_repo4 do
       build_gem "myrack", "1.0"
@@ -1696,6 +1696,7 @@ RSpec.describe "bundle update --bundler" do
       gem "myrack"
     G
 
+    system_gems "bundler-9.0.0.dev", path: local_gem_path
     bundle :update, bundler: "9.0.0.dev", verbose: "true"
 
     checksums = checksums_section_when_enabled do |c|
@@ -1722,7 +1723,7 @@ RSpec.describe "bundle update --bundler" do
   end
 
   it "does not touch the network if not necessary" do
-    system_gems "bundler-9.9.9", "bundler-9.0.0"
+    system_gems "bundler-9.9.9"
 
     build_repo4 do
       build_gem "myrack", "1.0"
@@ -1732,7 +1733,7 @@ RSpec.describe "bundle update --bundler" do
       source "https://gem.repo4"
       gem "myrack"
     G
-
+    system_gems "bundler-9.0.0", path: local_gem_path
     bundle :update, bundler: "9.0.0", verbose: true
 
     expect(out).not_to include("Fetching gem metadata from https://rubygems.org/")