diff --git a/app/models/invitation_log.rb b/app/models/invitation_log.rb
index 83cb0f13e..199c34d6d 100644
--- a/app/models/invitation_log.rb
+++ b/app/models/invitation_log.rb
@@ -6,7 +6,7 @@ class InvitationLog < ApplicationRecord
   belongs_to :loggable, polymorphic: true
   belongs_to :initiator, class_name: 'Member', optional: true
   belongs_to :chapter, optional: true
-  has_many :entries, class_name: 'InvitationLogEntry', dependent: :destroy
+  has_many :entries, class_name: 'InvitationLogEntry', dependent: :destroy, autosave: false
 
   before_create :set_expires_at
 
diff --git a/app/services/invitation_logger.rb b/app/services/invitation_logger.rb
index fc81c31a0..9c5e31898 100644
--- a/app/services/invitation_logger.rb
+++ b/app/services/invitation_logger.rb
@@ -23,7 +23,7 @@ def log_success(member, invitation = nil)
     return unless @log
 
     entry = find_or_build_entry(member, invitation, :success)
-    return entry if entry.persisted?
+    return entry if entry.processed_at
 
     entry.assign_attributes(processed_at: Time.current)
     save_entry(entry, :success_count)
@@ -33,7 +33,7 @@ def log_failure(member, invitation, error)
     return unless @log
 
     entry = find_or_build_entry(member, invitation, :failed)
-    return entry if entry.persisted?
+    return entry if entry.processed_at
 
     entry.assign_attributes(
       failure_reason: error.message,
@@ -46,7 +46,7 @@ def log_skipped(member, invitation, reason)
     return unless @log
 
     entry = find_or_build_entry(member, invitation, :skipped)
-    return entry if entry.persisted?
+    return entry if entry.processed_at
 
     entry.assign_attributes(
       failure_reason: reason,
@@ -78,11 +78,9 @@ def fail_batch(error)
   private
 
   def find_or_build_entry(member, invitation, status)
-    @log.entries.find_or_initialize_by(
-      member:,
-      invitation:,
-      status:
-    )
+    @log.entries.find_or_create_by(member: member, invitation: invitation) do |entry|
+      entry.status = status
+    end
   end
 
   def save_entry(entry, counter)
diff --git a/spec/services/invitation_logger_spec.rb b/spec/services/invitation_logger_spec.rb
index 14cd4b3c9..6595009d8 100644
--- a/spec/services/invitation_logger_spec.rb
+++ b/spec/services/invitation_logger_spec.rb
@@ -129,4 +129,32 @@
       expect(log.completed_at).to be_present
     end
   end
+
+  describe 'cross-status retry (PR #2558 fix)' do
+    let(:logger) { described_class.new(workshop, initiator, 'students', :invite) }
+    let!(:log) { logger.start_batch }
+
+    it 'returns existing failure entry when logging success for same member+invitation' do
+      error = StandardError.new('SMTP error')
+      failure_entry = logger.log_failure(member, invitation, error)
+
+      success_entry = logger.log_success(member, invitation)
+
+      expect(success_entry).to eq failure_entry
+      expect(success_entry.status).to eq 'failed'
+      expect(log.reload.success_count).to eq 0
+      expect(log.reload.failure_count).to eq 1
+    end
+
+    it 'returns existing success entry when logging failure for same member+invitation' do
+      logger.log_success(member, invitation)
+
+      error = StandardError.new('SMTP error')
+      failure_entry = logger.log_failure(member, invitation, error)
+
+      expect(failure_entry.status).to eq 'success'
+      expect(log.reload.success_count).to eq 1
+      expect(log.reload.failure_count).to eq 0
+    end
+  end
 end