diff --git a/lib/assigner.rb b/lib/assigner.rb
index eecf536a..f18b5867 100644
--- a/lib/assigner.rb
+++ b/lib/assigner.rb
@@ -195,7 +195,7 @@ def first_post
     topic.posts.where(post_number: 1).first
   end
 
-  def forbidden_reasons(assign_to:, type:, note:, status:)
+  def forbidden_reasons(assign_to:, type:, note:, status:, allow_self_reassign:)
     case
     when assign_to.is_a?(User) && !can_assignee_see_target?(assign_to)
       if topic.private_message?
@@ -211,7 +211,7 @@ def forbidden_reasons(assign_to:, type:, note:, status:)
       end
     when !can_be_assigned?(assign_to)
       assign_to.is_a?(User) ? :forbidden_assign_to : :forbidden_group_assign_to
-    when already_assigned?(assign_to, type, note, status)
+    when !allow_self_reassign && already_assigned?(assign_to, type, note, status)
       assign_to.is_a?(User) ? :already_assigned : :group_already_assigned
     when Assignment.where(topic: topic, active: true).count >= ASSIGNMENTS_PER_TOPIC_LIMIT &&
            !reassign?
@@ -252,7 +252,13 @@ def update_details(assign_to, note, status, skip_small_action_post: false)
     { success: true }
   end
 
-  def assign(assign_to, note: nil, skip_small_action_post: false, status: nil)
+  def assign(
+    assign_to,
+    note: nil,
+    skip_small_action_post: false,
+    status: nil,
+    allow_self_reassign: false
+  )
     assigned_to_type = assign_to.is_a?(User) ? "User" : "Group"
 
     if topic.private_message? && SiteSetting.invite_on_assign
@@ -260,7 +266,13 @@ def assign(assign_to, note: nil, skip_small_action_post: false, status: nil)
     end
 
     forbidden_reason =
-      forbidden_reasons(assign_to: assign_to, type: assigned_to_type, note: note, status: status)
+      forbidden_reasons(
+        assign_to: assign_to,
+        type: assigned_to_type,
+        note: note,
+        status: status,
+        allow_self_reassign: allow_self_reassign,
+      )
     return { success: false, reason: forbidden_reason } if forbidden_reason
 
     if no_assignee_change?(assign_to) && details_change?(note, status)
@@ -271,7 +283,8 @@ def assign(assign_to, note: nil, skip_small_action_post: false, status: nil)
     action_code[:user] = topic.assignment.present? ? "reassigned" : "assigned"
     action_code[:group] = topic.assignment.present? ? "reassigned_group" : "assigned_group"
 
-    skip_small_action_post = skip_small_action_post || no_assignee_change?(assign_to)
+    skip_small_action_post =
+      skip_small_action_post || (!allow_self_reassign && no_assignee_change?(assign_to))
 
     if @target.assignment
       Jobs.enqueue(
diff --git a/lib/random_assign_utils.rb b/lib/random_assign_utils.rb
index badfacd4..470f96af 100644
--- a/lib/random_assign_utils.rb
+++ b/lib/random_assign_utils.rb
@@ -87,7 +87,7 @@ def assign_user!
     return create_post_template if post_template
     Assigner
       .new(topic, Discourse.system_user)
-      .assign(assigned_user)
+      .assign(assigned_user, allow_self_reassign: true)
       .then do |result|
         next if result[:success]
         no_one!
@@ -104,7 +104,7 @@ def create_post_template
       ).create!
     Assigner
       .new(post, Discourse.system_user)
-      .assign(assigned_user)
+      .assign(assigned_user, allow_self_reassign: true)
       .then do |result|
         next if result[:success]
         PostDestroyer.new(Discourse.system_user, post).destroy
diff --git a/spec/lib/assigner_spec.rb b/spec/lib/assigner_spec.rb
index 265661ef..fb2b8f58 100644
--- a/spec/lib/assigner_spec.rb
+++ b/spec/lib/assigner_spec.rb
@@ -264,33 +264,47 @@ def assigned_to?(assignee)
         expect(second_assign[:success]).to eq(true)
       end
 
-      it "fails to assign when the assigned user and note is the same" do
-        assigner = described_class.new(topic, moderator_2)
-        assigner.assign(moderator, note: "note me down")
+      context "when 'allow_self_reassign' is false" do
+        subject(:assign) do
+          assigner.assign(moderator, note: other_note, allow_self_reassign: self_reassign)
+        end
 
-        assign = assigner.assign(moderator, note: "note me down")
+        let(:self_reassign) { false }
+        let(:assigner) { described_class.new(topic, moderator_2) }
+        let(:note) { "note me down" }
 
-        expect(assign[:success]).to eq(false)
-        expect(assign[:reason]).to eq(:already_assigned)
-      end
+        before { assigner.assign(moderator, note: note) }
 
-      it "fails to assign when the assigned user and note is the same" do
-        assigner = described_class.new(post, moderator_2)
-        assigner.assign(moderator, note: "note me down")
+        context "when the assigned user and the note is the same" do
+          let(:other_note) { note }
 
-        assign = assigner.assign(moderator, note: "note me down")
+          it "fails to assign" do
+            expect(assign).to match(success: false, reason: :already_assigned)
+          end
+        end
 
-        expect(assign[:success]).to eq(false)
-        expect(assign[:reason]).to eq(:already_assigned)
+        context "when the assigned user is the same but the note is different" do
+          let(:other_note) { "note me down again" }
+
+          it "allows assignment" do
+            expect(assign).to match(success: true)
+          end
+        end
       end
 
-      it "allows assign when the assigned user is same but note is different" do
-        assigner = described_class.new(topic, moderator_2)
-        assigner.assign(moderator, note: "note me down")
+      context "when 'allow_self_reassign' is true" do
+        subject(:assign) { assigner.assign(moderator, allow_self_reassign: self_reassign) }
 
-        assign = assigner.assign(moderator, note: "note me down again")
+        let(:self_reassign) { true }
+        let(:assigner) { described_class.new(topic, moderator_2) }
 
-        expect(assign[:success]).to eq(true)
+        context "when the assigned user is the same" do
+          before { assigner.assign(moderator) }
+
+          it "allows assignment" do
+            expect(assign).to match(success: true)
+          end
+        end
       end
 
       it "fails to assign when the assigned user cannot view the pm" do
diff --git a/spec/lib/random_assign_utils_spec.rb b/spec/lib/random_assign_utils_spec.rb
index 5e70ed49..6c99d168 100644
--- a/spec/lib/random_assign_utils_spec.rb
+++ b/spec/lib/random_assign_utils_spec.rb
@@ -182,6 +182,28 @@
       end
     end
 
+    context "when in a group of one person" do
+      let(:fields) do
+        {
+          "assignees_group" => {
+            "value" => group_1.id,
+          },
+          "assigned_topic" => {
+            "value" => topic_1.id,
+          },
+        }
+      end
+
+      context "when user is already assigned" do
+        before { described_class.automation_script!(ctx, fields, automation) }
+
+        it "reassigns them" do
+          expect { auto_assign }.to change { topic_1.reload.assignment.id }
+          expect(topic_1.assignment.assigned_to).to eq(user_1)
+        end
+      end
+    end
+
     context "when assignees_group is not provided" do
       let(:fields) { { "assigned_topic" => { "value" => topic_1.id } } }