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/workers/question_worker.rb b/app/workers/question_worker.rb
index c30c98d4..5d10904f 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? && !user.profile.allow_long_questions
 
     false
   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 a09a1ff7..51a4f3de 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/question/create_spec.rb b/spec/lib/use_case/question/create_spec.rb
index 607123b3..47b80ea4 100644
--- a/spec/lib/use_case/question/create_spec.rb
+++ b/spec/lib/use_case/question/create_spec.rb
@@ -61,7 +61,7 @@ describe UseCase::Question::Create do
       let(:content) { "a" * 513 }
 
       it "raises an error" do
-        expect { subject }.to raise_error(ActiveRecord::RecordInvalid)
+        expect { subject }.to raise_error(Errors::QuestionTooLong)
       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