diff --git a/enterprise/app/models/enterprise/account.rb b/enterprise/app/models/enterprise/account.rb
index eda28712f..6adc7cc48 100644
--- a/enterprise/app/models/enterprise/account.rb
+++ b/enterprise/app/models/enterprise/account.rb
@@ -1,7 +1,7 @@
 module Enterprise::Account
-  # Transitional marker for the Captain V1 to V2 rollout. New cloud accounts get
-  # this marker so plan reconciliation can enable V2 for them without upgrading
-  # existing paid accounts. Remove once every account is migrated to V2.
+  # Transitional marker for the Captain V1 to V2 rollout. Set this to false only
+  # for accounts that must remain on V1 during paid plan reconciliation.
+  # Remove once every account is migrated to V2.
   CAPTAIN_V2_DEFAULT_ELIGIBLE = 'captain_v2_default_eligible'.freeze
 
   class << self
diff --git a/enterprise/app/services/enterprise/billing/reconcile_plan_features_service.rb b/enterprise/app/services/enterprise/billing/reconcile_plan_features_service.rb
index 435b1f3d1..119fa3ea0 100644
--- a/enterprise/app/services/enterprise/billing/reconcile_plan_features_service.rb
+++ b/enterprise/app/services/enterprise/billing/reconcile_plan_features_service.rb
@@ -37,7 +37,7 @@ class Enterprise::Billing::ReconcilePlanFeaturesService
 
   def perform
     account.disable_features(*PREMIUM_PLAN_FEATURES)
-    account.disable_features('captain_integration_v2') if default_plan?
+    account.disable_features('captain_integration_v2')
     account.enable_features(*current_plan_features)
     account.enable_features('captain_integration_v2') if captain_v2_default_eligible?
     account.enable_features(*manually_managed_features)
@@ -74,6 +74,6 @@ class Enterprise::Billing::ReconcilePlanFeaturesService
   end
 
   def captain_v2_default_eligible?
-    !default_plan? && account.internal_attributes[Enterprise::Account::CAPTAIN_V2_DEFAULT_ELIGIBLE] == true
+    !default_plan? && account.internal_attributes[Enterprise::Account::CAPTAIN_V2_DEFAULT_ELIGIBLE] != false
   end
 end
diff --git a/spec/enterprise/services/enterprise/billing/handle_stripe_event_service_spec.rb b/spec/enterprise/services/enterprise/billing/handle_stripe_event_service_spec.rb
index 5116e1ec3..080bd184c 100644
--- a/spec/enterprise/services/enterprise/billing/handle_stripe_event_service_spec.rb
+++ b/spec/enterprise/services/enterprise/billing/handle_stripe_event_service_spec.rb
@@ -221,13 +221,13 @@ describe Enterprise::Billing::HandleStripeEventService do
         end
       end
 
-      it 'does not enable Captain V2 for existing paid accounts during reconciliation' do
+      it 'enables Captain V2 for existing paid accounts during reconciliation' do
         allow(subscription).to receive(:[]).with('plan')
                                            .and_return({ 'id' => 'test', 'product' => 'plan_id_startups', 'name' => 'Startups' })
 
         stripe_event_service.new.perform(event: event)
 
-        expect(account.reload).not_to be_feature_enabled('captain_integration_v2')
+        expect(account.reload).to be_feature_enabled('captain_integration_v2')
       end
 
       it 'enables Captain V2 for new cloud accounts marked as default eligible' do
@@ -243,6 +243,21 @@ describe Enterprise::Billing::HandleStripeEventService do
 
         expect(account.reload).to be_feature_enabled('captain_integration_v2')
       end
+
+      it 'disables Captain V2 for accounts explicitly held on V1' do
+        account.enable_features!('captain_integration_v2')
+        account.update!(
+          internal_attributes: account.internal_attributes.merge(
+            Enterprise::Account::CAPTAIN_V2_DEFAULT_ELIGIBLE => false
+          )
+        )
+        allow(subscription).to receive(:[]).with('plan')
+                                           .and_return({ 'id' => 'test', 'product' => 'plan_id_startups', 'name' => 'Startups' })
+
+        stripe_event_service.new.perform(event: event)
+
+        expect(account.reload).not_to be_feature_enabled('captain_integration_v2')
+      end
     end
 
     context 'with Business plan' do