diff --git a/app/controllers/settings/profile_controller.rb b/app/controllers/settings/profile_controller.rb
index 2d1576dd..75091ed0 100644
--- a/app/controllers/settings/profile_controller.rb
+++ b/app/controllers/settings/profile_controller.rb
@@ -6,7 +6,7 @@ class Settings::ProfileController < ApplicationController
   def edit; end
 
   def update
-    profile_attributes = params.require(:profile).permit(:display_name, :motivation_header, :website, :location, :description, :anon_display_name)
+    profile_attributes = params.require(:profile).permit(:display_name, :motivation_header, :website, :location, :description, :anon_display_name, :allow_long_questions)
 
     if current_user.profile.update(profile_attributes)
       flash[:success] = t(".success")
diff --git a/app/javascript/retrospring/controllers/character_count_warning_controller.ts b/app/javascript/retrospring/controllers/character_count_warning_controller.ts
new file mode 100644
index 00000000..8c1bfe07
--- /dev/null
+++ b/app/javascript/retrospring/controllers/character_count_warning_controller.ts
@@ -0,0 +1,30 @@
+import { Controller } from '@hotwired/stimulus';
+
+export default class extends Controller {
+  static targets = ['input', 'warning'];
+
+  declare readonly inputTarget: HTMLInputElement;
+  declare readonly warningTarget: HTMLElement;
+
+  static values = {
+    warn: Number
+  };
+
+  declare readonly warnValue: number;
+
+  connect(): void {
+    this.inputTarget.addEventListener('input', this.update.bind(this));
+  }
+
+  update(): void {
+    if (this.inputTarget.value.length > this.warnValue) {
+      if (this.warningTarget.classList.contains('d-none')) {
+        this.warningTarget.classList.remove('d-none');
+      }
+    } else {
+      if (!this.warningTarget.classList.contains('d-none')) {
+        this.warningTarget.classList.add('d-none');
+      }
+    }
+  }
+}
diff --git a/app/javascript/retrospring/features/questionbox/all.ts b/app/javascript/retrospring/features/questionbox/all.ts
index a7d6a3b8..4a1373f4 100644
--- a/app/javascript/retrospring/features/questionbox/all.ts
+++ b/app/javascript/retrospring/features/questionbox/all.ts
@@ -24,10 +24,6 @@ export function questionboxAllHandler(event: Event): void {
         document.querySelector<HTMLInputElement>('textarea[name=qb-all-question]').value = '';
         const modal = Modal.getInstance(document.querySelector('#modal-ask-followers'));
         modal.hide();
-
-        // FIXME: also solve this using a Stimulus controller
-        const characterCount = document.querySelector<HTMLElement>('#modal-ask-followers [data-character-count-max-value]').dataset.characterCountMaxValue;
-        document.querySelector<HTMLElement>('#modal-ask-followers [data-character-count-target="counter"]').innerHTML = characterCount;
       }
 
       showNotification(data.message, data.success);
diff --git a/app/javascript/retrospring/features/questionbox/user.ts b/app/javascript/retrospring/features/questionbox/user.ts
index d398c70f..5fa3cbf9 100644
--- a/app/javascript/retrospring/features/questionbox/user.ts
+++ b/app/javascript/retrospring/features/questionbox/user.ts
@@ -30,8 +30,10 @@ export function questionboxUserHandler(event: Event): void {
         document.querySelector<HTMLInputElement>('textarea[name=qb-question]').value = '';
 
         // FIXME: also solve this using a Stimulus controller
-        const characterCount = document.querySelector<HTMLElement>('#question-box[data-character-count-max-value]').dataset.characterCountMaxValue;
-        document.querySelector<HTMLElement>('#question-box [data-character-count-target="counter"]').innerHTML = characterCount;
+        const questionBox = document.getElementById('question-box');
+        if ('characterCountMaxValue' in questionBox.dataset) {
+          questionBox.querySelector<HTMLElement>('[data-character-count-target="counter"]').innerHTML = questionBox.dataset.characterCountMaxValue;
+        }
 
         if (promote) {
           const questionbox = document.querySelector('#question-box');
diff --git a/app/javascript/retrospring/initializers/stimulus.ts b/app/javascript/retrospring/initializers/stimulus.ts
index 0c5c43de..90b3a96d 100644
--- a/app/javascript/retrospring/initializers/stimulus.ts
+++ b/app/javascript/retrospring/initializers/stimulus.ts
@@ -2,6 +2,7 @@ import { Application } from "@hotwired/stimulus";
 import AnnouncementController from "retrospring/controllers/announcement_controller";
 import AutofocusController from "retrospring/controllers/autofocus_controller";
 import CharacterCountController from "retrospring/controllers/character_count_controller";
+import CharacterCountWarningController from "retrospring/controllers/character_count_warning_controller";
 import FormatPopupController from "retrospring/controllers/format_popup_controller";
 
 /**
@@ -16,5 +17,6 @@ export default function (): void {
   window['Stimulus'].register('announcement', AnnouncementController);
   window['Stimulus'].register('autofocus', AutofocusController);
   window['Stimulus'].register('character-count', CharacterCountController);
+  window['Stimulus'].register('character-count-warning', CharacterCountWarningController);
   window['Stimulus'].register('format-popup', FormatPopupController);
 }
diff --git a/app/models/profile.rb b/app/models/profile.rb
index df75ce61..b2927860 100644
--- a/app/models/profile.rb
+++ b/app/models/profile.rb
@@ -26,4 +26,6 @@ class Profile < ApplicationRecord
   def safe_name
     display_name.presence || user.screen_name
   end
+
+  def question_length_limit = allow_long_questions ? nil : Question::SHORT_QUESTION_MAX_LENGTH
 end
diff --git a/app/models/question.rb b/app/models/question.rb
index 88b5565c..0a6adec0 100644
--- a/app/models/question.rb
+++ b/app/models/question.rb
@@ -5,7 +5,9 @@ class Question < ApplicationRecord
   has_many :answers, dependent: :destroy
   has_many :inboxes, dependent: :destroy
 
-  validates :content, length: { minimum: 1, maximum: 512 }
+  validates :content, length: { minimum: 1 }
+
+  SHORT_QUESTION_MAX_LENGTH = 512
 
   before_destroy do
     rep = Report.where(target_id: self.id, type: 'Reports::Question')
@@ -30,4 +32,6 @@ class Question < ApplicationRecord
   def generated? = %w[justask retrospring_exporter].include?(author_identifier)
 
   def anonymous? = author_is_anonymous && author_identifier.present?
+
+  def long? = content.length > SHORT_QUESTION_MAX_LENGTH
 end
diff --git a/app/views/application/_questionbox.html.haml b/app/views/application/_questionbox.html.haml
index 42c0731e..d56fefda 100644
--- a/app/views/application/_questionbox.html.haml
+++ b/app/views/application/_questionbox.html.haml
@@ -22,7 +22,7 @@
         %strong= t(".status.require_user_html", sign_in: link_to(t("voc.login"), new_user_session_path), sign_up: link_to(t("voc.register"), new_user_registration_path))
     - else
       - if user_signed_in? || user.privacy_allow_anonymous_questions?
-        #question-box{ data: { controller: "character-count", "character-count-max-value": 512 }}
+        #question-box{ data: user.profile.allow_long_questions ? {} : { controller: "character-count", "character-count-max-value": user.profile.question_length_limit }}
           %textarea.form-control{ name: "qb-question", placeholder: t(".placeholder"), data: { "character-count-target": "input" } }
           .row{ style: "padding-top: 5px;" }
             .col-6
@@ -36,7 +36,7 @@
                   %input{ name: "qb-anonymous", type: :hidden, value: false }/
             .col-6
               %p.pull-right
-                %span.text-muted.me-1{ data: { "character-count-target": "counter" } } 512
+                %span.text-muted.me-1{ class: user.profile.allow_long_questions ? "d-none" : "", data: { "character-count-target": "counter" } }= Question::SHORT_QUESTION_MAX_LENGTH
                 %input{ name: "qb-to", type: "hidden", value: user.id }/
                 %button.btn.btn-primary{ name: "qb-ask",
                   type: :button,
diff --git a/app/views/modal/_ask.html.haml b/app/views/modal/_ask.html.haml
index 740a684a..00192b61 100644
--- a/app/views/modal/_ask.html.haml
+++ b/app/views/modal/_ask.html.haml
@@ -1,14 +1,14 @@
 .modal.fade#modal-ask-followers{ aria: { hidden: true, labelledby: "modal-ask-followers-label" }, role: :dialog, tabindex: -1 }
   .modal-dialog
-    .modal-content{ data: { controller: "character-count", "character-count-max-value": 512 }}
+    .modal-content{ data: { controller: "character-count-warning", "character-count-warning-warn-value": Question::SHORT_QUESTION_MAX_LENGTH }}
       .modal-header
         %h5.modal-title#modal-ask-followers-label= t(".title")
         %button.btn-close{ data: { bs_dismiss: :modal }, type: :button }
           %span.visually-hidden= t("voc.close")
       .modal-body
         .form-group.has-feedback
-          %textarea.form-control{ name: "qb-all-question", placeholder: t(".placeholder"), data: { "character-count-target": "input" } }
-          %p.text-end.text-muted.form-control-feedback{ data: { "character-count-target": "counter" } } 512
+          %textarea.form-control{ name: "qb-all-question", placeholder: t(".placeholder"), data: { "character-count-warning-target": "input" } }
+          .alert.alert-warning.mt-3.d-none{ data: { "character-count-warning-target": "warning" } }= t('.long_question_warning')
       .modal-footer
         %button.btn.btn-default{ type: :button, data: { bs_dismiss: :modal } }= t("voc.cancel")
-        %button.btn.btn-primary{ name: "qb-all-ask", type: :button, data: { "character-count-target": "action", loading_text: t(".loading") } }= t(".action")
+        %button.btn.btn-primary{ name: "qb-all-ask", type: :button, data: { loading_text: t(".loading") } }= t(".action")
diff --git a/app/views/settings/profile/edit.html.haml b/app/views/settings/profile/edit.html.haml
index 1f8240d4..7cd29926 100644
--- a/app/views/settings/profile/edit.html.haml
+++ b/app/views/settings/profile/edit.html.haml
@@ -49,6 +49,8 @@
 
       = f.text_area :description
 
+      = f.check_box :allow_long_questions
+
       = f.primary
 
 - provide(:title, generate_title(t(".title")))
diff --git a/app/workers/question_worker.rb b/app/workers/question_worker.rb
index c30c98d4..969b725f 100644
--- a/app/workers/question_worker.rb
+++ b/app/workers/question_worker.rb
@@ -30,6 +30,7 @@ class QuestionWorker
     return true if follower.banned?
     return true if muted?(follower, question)
     return true if user.muting?(question.user)
+    return true if question.long? && !follower.profile.allow_long_questions
 
     false
   end
diff --git a/config/locales/views.en.yml b/config/locales/views.en.yml
index 583c0616..e1696485 100644
--- a/config/locales/views.en.yml
+++ b/config/locales/views.en.yml
@@ -254,6 +254,7 @@ en:
       placeholder: "Type your question here…"
       action: "Ask"
       loading: "Asking…"
+      long_question_warning: "This question will only be sent to those who allow long questions in their profile settings."
     comment_smiles:
       title: "People who smiled this comment"
       none: "No one has smiled this comment yet."
diff --git a/db/migrate/20230108114333_add_allow_long_questions_to_profiles.rb b/db/migrate/20230108114333_add_allow_long_questions_to_profiles.rb
new file mode 100644
index 00000000..5f67a004
--- /dev/null
+++ b/db/migrate/20230108114333_add_allow_long_questions_to_profiles.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class AddAllowLongQuestionsToProfiles < ActiveRecord::Migration[6.1]
+  def change
+    add_column :profiles, :allow_long_questions, :boolean, default: false
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 05514255..45b1005d 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema.define(version: 2022_12_27_065923) do
+ActiveRecord::Schema.define(version: 2023_01_08_114333) do
 
   # These are extensions that must be enabled in order to support this database
   enable_extension "plpgsql"
@@ -134,6 +134,7 @@ ActiveRecord::Schema.define(version: 2022_12_27_065923) do
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.string "anon_display_name"
+    t.boolean "allow_long_questions", default: false
     t.index ["user_id"], name: "index_profiles_on_user_id"
   end
 
diff --git a/lib/errors.rb b/lib/errors.rb
index 314ed4bc..5e2586c8 100644
--- a/lib/errors.rb
+++ b/lib/errors.rb
@@ -28,6 +28,9 @@ module Errors
   class InvalidBanDuration < BadRequest
   end
 
+  class QuestionTooLong < BadRequest
+  end
+
   class Forbidden < Base
     def status
       403
diff --git a/lib/use_case/question/create.rb b/lib/use_case/question/create.rb
index baca5c89..5cc8f174 100644
--- a/lib/use_case/question/create.rb
+++ b/lib/use_case/question/create.rb
@@ -63,6 +63,7 @@ module UseCase
 
       def check_user
         raise Errors::NotAuthorized if target_user.privacy_require_user && !source_user_id
+        raise Errors::QuestionTooLong if content.length > ::Question::SHORT_QUESTION_MAX_LENGTH && !target_user.profile.allow_long_questions
       end
 
       def create_question
diff --git a/spec/lib/use_case/data_export/user_spec.rb b/spec/lib/use_case/data_export/user_spec.rb
index a8c692ea..f9c70ff9 100644
--- a/spec/lib/use_case/data_export/user_spec.rb
+++ b/spec/lib/use_case/data_export/user_spec.rb
@@ -27,11 +27,12 @@ describe UseCase::DataExport::User, :data_export do
       sign_in_count:                     10,
       smiled_count:                      28,
       profile:                           {
-        display_name:      "Fizzy Raccoon",
-        description:       "A small raccoon",
-        location:          "Binland",
-        motivation_header: "",
-        website:           "https://retrospring.net"
+        display_name:         "Fizzy Raccoon",
+        description:          "A small raccoon",
+        location:             "Binland",
+        motivation_header:    "",
+        website:              "https://retrospring.net",
+        allow_long_questions: true
       }
     }
   end
@@ -87,14 +88,15 @@ describe UseCase::DataExport::User, :data_export do
           privacy_noindex:                   false
         },
         profile: {
-          display_name:      "Fizzy Raccoon",
-          description:       "A small raccoon",
-          location:          "Binland",
-          website:           "https://retrospring.net",
-          motivation_header: "",
-          created_at:        user.profile.created_at.as_json,
-          updated_at:        user.profile.updated_at.as_json,
-          anon_display_name: nil
+          display_name:         "Fizzy Raccoon",
+          description:          "A small raccoon",
+          location:             "Binland",
+          website:              "https://retrospring.net",
+          motivation_header:    "",
+          created_at:           user.profile.created_at.as_json,
+          updated_at:           user.profile.updated_at.as_json,
+          anon_display_name:    nil,
+          allow_long_questions: true
         },
         roles:   {
           administrator: false,
diff --git a/spec/lib/use_case/question/create_spec.rb b/spec/lib/use_case/question/create_spec.rb
index 607123b3..a1831771 100644
--- a/spec/lib/use_case/question/create_spec.rb
+++ b/spec/lib/use_case/question/create_spec.rb
@@ -57,11 +57,22 @@ describe UseCase::Question::Create do
       end
     end
 
-    context "content is too long" do
+    context "content is over 512 characters long" do
       let(:content) { "a" * 513 }
 
-      it "raises an error" do
-        expect { subject }.to raise_error(ActiveRecord::RecordInvalid)
+      context "recipient does not allow long questions" do
+        it "raises an error" do
+          expect { subject }.to raise_error(Errors::QuestionTooLong)
+        end
+      end
+
+      context "recipient allows long questions" do
+        before do
+          target_user.profile.allow_long_questions = true
+          target_user.profile.save
+        end
+
+        it_behaves_like "creates the question"
       end
     end
   end
diff --git a/spec/models/question_spec.rb b/spec/models/question_spec.rb
index 2e88fc42..7da9eab0 100644
--- a/spec/models/question_spec.rb
+++ b/spec/models/question_spec.rb
@@ -16,11 +16,6 @@ RSpec.describe Question, :type => :model do
     expect(@question.content).to match 'Is this a question?'
   end
 
-  it 'does not save questions longer than 512 characters' do
-    @question.content = 'X' * 513
-    expect{@question.save!}.to raise_error(ActiveRecord::RecordInvalid)
-  end
-
   it 'has many answers' do
     5.times { |i| Answer.create(content: "This is an answer. #{i}", user: FactoryBot.create(:user), question: @question) }
     expect(@question.answer_count).to match 5
diff --git a/spec/workers/question_worker_spec.rb b/spec/workers/question_worker_spec.rb
index cf022124..8070392b 100644
--- a/spec/workers/question_worker_spec.rb
+++ b/spec/workers/question_worker_spec.rb
@@ -6,7 +6,8 @@ describe QuestionWorker do
   describe "#perform" do
     let(:user) { FactoryBot.create(:user) }
     let(:user_id) { user.id }
-    let(:question) { FactoryBot.create(:question, user:) }
+    let(:content) { Faker::Lorem.sentence }
+    let(:question) { FactoryBot.create(:question, content:, user:) }
     let(:question_id) { question.id }
 
     before do
@@ -92,5 +93,20 @@ describe QuestionWorker do
           )
       end
     end
+
+    context "long question" do
+      let(:content) { "x" * 1000 }
+
+      it "sends to recipients who allow long questions" do
+        user.followers.first.profile.update(allow_long_questions: true)
+
+        expect { subject }
+          .to(
+            change { Inbox.where(user_id: user.followers.ids, question_id:, new: true).count }
+              .from(0)
+              .to(1)
+          )
+      end
+    end
   end
 end