diff --git a/app/assets/javascripts/discourse/app/controllers/bookmark.js b/app/assets/javascripts/discourse/app/controllers/bookmark.js
index 992c3228a02..7d86ed2b74a 100644
--- a/app/assets/javascripts/discourse/app/controllers/bookmark.js
+++ b/app/assets/javascripts/discourse/app/controllers/bookmark.js
@@ -1,4 +1,5 @@
 import { and } from "@ember/object/computed";
+import { next } from "@ember/runloop";
 import { action } from "@ember/object";
 import { isPresent } from "@ember/utils";
 import Controller from "@ember/controller";
@@ -59,6 +60,8 @@ export default Controller.extend(ModalFunctionality, {
   lastCustomReminderTime: null,
   mouseTrap: null,
   userTimezone: null,
+  showOptions: false,
+  options: null,
 
   onShow() {
     this.setProperties({
@@ -70,9 +73,13 @@ export default Controller.extend(ModalFunctionality, {
       customReminderTime: this._defaultCustomReminderTime(),
       lastCustomReminderDate: null,
       lastCustomReminderTime: null,
-      userTimezone: this.currentUser.resolvedTimezone()
+      userTimezone: this.currentUser.resolvedTimezone(),
+      showOptions: false,
+      options: {},
+      model: this.model || {}
     });
 
+    this._loadBookmarkOptions();
     this._bindKeyboardShortcuts();
     this._loadLastUsedCustomReminderDatetime();
 
@@ -124,6 +131,21 @@ export default Controller.extend(ModalFunctionality, {
     return isPresent(this.model) && isPresent(this.model.reminderAt);
   },
 
+  _loadBookmarkOptions() {
+    this.set(
+      "options.deleteWhenReminderSent",
+      this.model.deleteWhenReminderSent ||
+        localStorage.bookmarkOptionsDeleteWhenReminderSent === "true"
+    );
+
+    // we want to make sure the options panel opens so the user
+    // knows they have set these options previously. run next otherwise
+    // the modal is not visible when it tries to slide down the options
+    if (this.options.deleteWhenReminderSent) {
+      next(() => this.toggleOptionsPanel());
+    }
+  },
+
   _loadLastUsedCustomReminderDatetime() {
     let lastTime = localStorage.lastCustomBookmarkReminderTime;
     let lastDate = localStorage.lastCustomBookmarkReminderDate;
@@ -268,6 +290,8 @@ export default Controller.extend(ModalFunctionality, {
       localStorage.lastCustomBookmarkReminderDate = this.customReminderDate;
     }
 
+    localStorage.bookmarkOptionsDeleteWhenReminderSent = this.options.deleteWhenReminderSent;
+
     let reminderType;
     if (this.selectedReminderType === REMINDER_TYPES.NONE) {
       reminderType = null;
@@ -282,7 +306,8 @@ export default Controller.extend(ModalFunctionality, {
       reminder_at: reminderAtISO,
       name: this.model.name,
       post_id: this.model.postId,
-      id: this.model.id
+      id: this.model.id,
+      delete_when_reminder_sent: this.options.deleteWhenReminderSent
     };
 
     if (this._editingExistingBookmark()) {
@@ -294,6 +319,7 @@ export default Controller.extend(ModalFunctionality, {
           this.afterSave({
             reminderAt: reminderAtISO,
             reminderType: this.selectedReminderType,
+            deleteWhenReminderSent: this.options.deleteWhenReminderSent,
             id: this.model.id,
             name: this.model.name
           });
@@ -305,6 +331,7 @@ export default Controller.extend(ModalFunctionality, {
           this.afterSave({
             reminderAt: reminderAtISO,
             reminderType: this.selectedReminderType,
+            deleteWhenReminderSent: this.options.deleteWhenReminderSent,
             id: response.id,
             name: this.model.name
           });
@@ -420,6 +447,16 @@ export default Controller.extend(ModalFunctionality, {
     }
   },
 
+  @action
+  toggleOptionsPanel() {
+    if (this.showOptions) {
+      $(".bookmark-options-panel").slideUp("fast");
+    } else {
+      $(".bookmark-options-panel").slideDown("fast");
+    }
+    this.toggleProperty("showOptions");
+  },
+
   @action
   saveAndClose() {
     if (this._saving || this._deleting) {
diff --git a/app/assets/javascripts/discourse/app/models/post.js b/app/assets/javascripts/discourse/app/models/post.js
index e7cf6028e57..e0565b420c0 100644
--- a/app/assets/javascripts/discourse/app/models/post.js
+++ b/app/assets/javascripts/discourse/app/models/post.js
@@ -316,6 +316,7 @@ const Post = RestModel.extend({
           postId: this.id,
           id: this.bookmark_id,
           reminderAt: this.bookmark_reminder_at,
+          deleteWhenReminderSent: this.bookmark_delete_when_reminder_sent,
           name: this.bookmark_name
         },
         title: this.bookmark_id
@@ -334,6 +335,8 @@ const Post = RestModel.extend({
             bookmarked: true,
             bookmark_reminder_at: savedData.reminderAt,
             bookmark_reminder_type: savedData.reminderType,
+            bookmark_delete_when_reminder_sent:
+              savedData.deleteWhenReminderSent,
             bookmark_name: savedData.name,
             bookmark_id: savedData.id
           });
diff --git a/app/assets/javascripts/discourse/app/templates/modal/bookmark.hbs b/app/assets/javascripts/discourse/app/templates/modal/bookmark.hbs
index 2cac81e9b65..b69713e7570 100644
--- a/app/assets/javascripts/discourse/app/templates/modal/bookmark.hbs
+++ b/app/assets/javascripts/discourse/app/templates/modal/bookmark.hbs
@@ -8,8 +8,16 @@
       </div>
     {{/if}}
 
-    <div class="control-group">
+    <div class="control-group bookmark-name-wrap">
       {{input id="bookmark-name" value=model.name name="name" class="bookmark-name" placeholder=(i18n "post.bookmarks.name_placeholder")}}
+      {{d-button icon="gear" action=(action "toggleOptionsPanel") class="bookmark-options-button"}}
+    </div>
+
+    <div class="bookmark-options-panel">
+      <label for="delete_when_reminder_sent">
+        {{i18n "bookmarks.delete_when_reminder_sent"}}
+        {{input id="delete_when_reminder_sent" type="checkbox" checked=options.deleteWhenReminderSent}}
+      </label>
     </div>
 
     {{#if showExistingReminderAt }}
diff --git a/app/assets/stylesheets/common/components/bookmark-modal.scss b/app/assets/stylesheets/common/components/bookmark-modal.scss
index 45ad12fc189..b870ec00d1e 100644
--- a/app/assets/stylesheets/common/components/bookmark-modal.scss
+++ b/app/assets/stylesheets/common/components/bookmark-modal.scss
@@ -62,4 +62,24 @@
       flex: 1 1 auto;
     }
   }
+
+  .bookmark-name-wrap {
+    display: inline-flex;
+    width: 100%;
+    align-items: end;
+  }
+
+  .bookmark-options-button {
+    margin-left: 0.5em;
+    background: transparent;
+  }
+
+  .bookmark-options-panel {
+    margin-bottom: 18px;
+    display: none;
+
+    input[type="checkbox"] {
+      margin-right: 0.85em;
+    }
+  }
 }
diff --git a/app/controllers/bookmarks_controller.rb b/app/controllers/bookmarks_controller.rb
index f7fed51f59b..001e75c119b 100644
--- a/app/controllers/bookmarks_controller.rb
+++ b/app/controllers/bookmarks_controller.rb
@@ -11,7 +11,10 @@ class BookmarksController < ApplicationController
       post_id: params[:post_id],
       name: params[:name],
       reminder_type: params[:reminder_type],
-      reminder_at: params[:reminder_at]
+      reminder_at: params[:reminder_at],
+      options: {
+        delete_when_reminder_sent: params[:delete_when_reminder_sent]
+      }
     )
 
     if bookmark_manager.errors.empty?
@@ -35,7 +38,10 @@ class BookmarksController < ApplicationController
       bookmark_id: params[:id],
       name: params[:name],
       reminder_type: params[:reminder_type],
-      reminder_at: params[:reminder_at]
+      reminder_at: params[:reminder_at],
+      options: {
+        delete_when_reminder_sent: params[:delete_when_reminder_sent]
+      }
     )
 
     if bookmark_manager.errors.empty?
diff --git a/app/models/bookmark.rb b/app/models/bookmark.rb
index 3cfae4fe174..3125f8f9fed 100644
--- a/app/models/bookmark.rb
+++ b/app/models/bookmark.rb
@@ -79,17 +79,18 @@ end
 #
 # Table name: bookmarks
 #
-#  id                    :bigint           not null, primary key
-#  user_id               :bigint           not null
-#  topic_id              :bigint           not null
-#  post_id               :bigint           not null
-#  name                  :string
-#  reminder_type         :integer
-#  reminder_at           :datetime
-#  created_at            :datetime         not null
-#  updated_at            :datetime         not null
-#  reminder_last_sent_at :datetime
-#  reminder_set_at       :datetime
+#  id                        :bigint           not null, primary key
+#  user_id                   :bigint           not null
+#  topic_id                  :bigint           not null
+#  post_id                   :bigint           not null
+#  name                      :string
+#  reminder_type             :integer
+#  reminder_at               :datetime
+#  created_at                :datetime         not null
+#  updated_at                :datetime         not null
+#  reminder_last_sent_at     :datetime
+#  reminder_set_at           :datetime
+#  delete_when_reminder_sent :boolean          default(FALSE)
 #
 # Indexes
 #
diff --git a/app/serializers/post_serializer.rb b/app/serializers/post_serializer.rb
index ef39e37caab..35a50a5f96f 100644
--- a/app/serializers/post_serializer.rb
+++ b/app/serializers/post_serializer.rb
@@ -53,6 +53,7 @@ class PostSerializer < BasicPostSerializer
              :bookmark_id,
              :bookmark_reminder_type,
              :bookmark_name,
+             :bookmark_delete_when_reminder_sent,
              :raw,
              :actions_summary,
              :moderator?,
@@ -331,6 +332,10 @@ class PostSerializer < BasicPostSerializer
     include_bookmarked?
   end
 
+  def include_bookmark_delete_when_reminder_sent?
+    include_bookmarked?
+  end
+
   def include_bookmark_id?
     include_bookmarked?
   end
@@ -353,6 +358,10 @@ class PostSerializer < BasicPostSerializer
     post_bookmark&.name
   end
 
+  def bookmark_delete_when_reminder_sent
+    post_bookmark&.delete_when_reminder_sent
+  end
+
   def bookmark_id
     post_bookmark&.id
   end
diff --git a/config/locales/client.en.yml b/config/locales/client.en.yml
index b4b6ad31f2a..e4a65a3b1e3 100644
--- a/config/locales/client.en.yml
+++ b/config/locales/client.en.yml
@@ -319,6 +319,7 @@ en:
       no_timezone: 'You have not set a timezone yet. You will not be able to set reminders. Set one up <a href="%{basePath}/my/preferences/profile">in your profile</a>.'
       invalid_custom_datetime: "The date and time you provided is invalid, please try again."
       list_permission_denied: "You do not have permission to view this user's bookmarks."
+      delete_when_reminder_sent: "Delete this bookmark when the reminder notification is sent."
       reminders:
         at_desktop: "Next time I'm at my desktop"
         later_today: "Later today"
diff --git a/db/migrate/20200505060712_add_delete_when_reminder_sent_boolean_to_bookmarks.rb b/db/migrate/20200505060712_add_delete_when_reminder_sent_boolean_to_bookmarks.rb
new file mode 100644
index 00000000000..7e4ca807fa3
--- /dev/null
+++ b/db/migrate/20200505060712_add_delete_when_reminder_sent_boolean_to_bookmarks.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class AddDeleteWhenReminderSentBooleanToBookmarks < ActiveRecord::Migration[6.0]
+  def change
+    add_column :bookmarks, :delete_when_reminder_sent, :boolean, nullabe: false, default: false
+  end
+end
diff --git a/lib/bookmark_manager.rb b/lib/bookmark_manager.rb
index 23328021f6a..90088181f63 100644
--- a/lib/bookmark_manager.rb
+++ b/lib/bookmark_manager.rb
@@ -7,20 +7,22 @@ class BookmarkManager
     @user = user
   end
 
-  def create(post_id:, name: nil, reminder_type: nil, reminder_at: nil)
+  def create(post_id:, name: nil, reminder_type: nil, reminder_at: nil, options: {})
     post = Post.unscoped.includes(:topic).find(post_id)
     reminder_type = parse_reminder_type(reminder_type)
 
     raise Discourse::InvalidAccess.new if !Guardian.new(@user).can_see_post?(post)
 
     bookmark = Bookmark.create(
-      user_id: @user.id,
-      topic: post.topic,
-      post: post,
-      name: name,
-      reminder_type: reminder_type,
-      reminder_at: reminder_at,
-      reminder_set_at: Time.zone.now
+      {
+        user_id: @user.id,
+        topic: post.topic,
+        post: post,
+        name: name,
+        reminder_type: reminder_type,
+        reminder_at: reminder_at,
+        reminder_set_at: Time.zone.now
+      }.merge(options)
     )
 
     if bookmark.errors.any?
@@ -66,7 +68,7 @@ class BookmarkManager
     BookmarkReminderNotificationHandler.send_notification(bookmark)
   end
 
-  def update(bookmark_id:, name:, reminder_type:, reminder_at:)
+  def update(bookmark_id:, name:, reminder_type:, reminder_at:, options: {})
     bookmark = Bookmark.find_by(id: bookmark_id)
 
     raise Discourse::NotFound if bookmark.blank?
@@ -75,10 +77,12 @@ class BookmarkManager
     reminder_type = parse_reminder_type(reminder_type)
 
     success = bookmark.update(
-      name: name,
-      reminder_at: reminder_at,
-      reminder_type: reminder_type,
-      reminder_set_at: Time.zone.now
+      {
+        name: name,
+        reminder_at: reminder_at,
+        reminder_type: reminder_type,
+        reminder_set_at: Time.zone.now
+      }.merge(options)
     )
 
     if bookmark.errors.any?
diff --git a/lib/bookmark_reminder_notification_handler.rb b/lib/bookmark_reminder_notification_handler.rb
index 223c55b2ac5..b1f32cee618 100644
--- a/lib/bookmark_reminder_notification_handler.rb
+++ b/lib/bookmark_reminder_notification_handler.rb
@@ -9,6 +9,11 @@ class BookmarkReminderNotificationHandler
       end
 
       create_notification(bookmark)
+
+      if bookmark.delete_when_reminder_sent?
+        return bookmark.destroy
+      end
+
       clear_reminder(bookmark)
     end
   end
diff --git a/spec/lib/bookmark_manager_spec.rb b/spec/lib/bookmark_manager_spec.rb
index d821e994465..24bdd6bd15c 100644
--- a/spec/lib/bookmark_manager_spec.rb
+++ b/spec/lib/bookmark_manager_spec.rb
@@ -42,6 +42,17 @@ RSpec.describe BookmarkManager do
       end
     end
 
+    context "when options are provided" do
+      let(:options) { { delete_when_reminder_sent: true } }
+
+      it "saves any additional options successfully" do
+        subject.create(post_id: post.id, name: name, options: options)
+        bookmark = Bookmark.find_by(user: user)
+
+        expect(bookmark.delete_when_reminder_sent).to eq(true)
+      end
+    end
+
     context "when the bookmark already exists for the user & post" do
       before do
         Bookmark.create(post: post, user: user, topic: post.topic)
@@ -142,14 +153,19 @@ RSpec.describe BookmarkManager do
     let(:new_name) { "Some new name" }
     let(:new_reminder_at) { 10.days.from_now }
     let(:new_reminder_type) { Bookmark.reminder_types[:custom] }
+    let(:options) { {} }
 
     def update_bookmark
       subject.update(
-        bookmark_id: bookmark.id, name: new_name, reminder_type: new_reminder_type, reminder_at: new_reminder_at
+        bookmark_id: bookmark.id,
+        name: new_name,
+        reminder_type: new_reminder_type,
+        reminder_at: new_reminder_at,
+        options: options
       )
     end
 
-    it "saves the time and new reminder type sucessfully" do
+    it "saves the time and new reminder type and new name sucessfully" do
       update_bookmark
       bookmark.reload
       expect(bookmark.name).to eq(new_name)
@@ -157,6 +173,16 @@ RSpec.describe BookmarkManager do
       expect(bookmark.reminder_type).to eq(new_reminder_type)
     end
 
+    context "when options are provided" do
+      let(:options) { { delete_when_reminder_sent: true } }
+
+      it "saves any additional options successfully" do
+        update_bookmark
+        bookmark.reload
+        expect(bookmark.delete_when_reminder_sent).to eq(true)
+      end
+    end
+
     context "if the new reminder type is a string" do
       let(:new_reminder_type) { "custom" }
       it "is parsed" do
diff --git a/spec/lib/bookmark_reminder_notification_handler_spec.rb b/spec/lib/bookmark_reminder_notification_handler_spec.rb
index d86ce73a5ed..6af860f2f04 100644
--- a/spec/lib/bookmark_reminder_notification_handler_spec.rb
+++ b/spec/lib/bookmark_reminder_notification_handler_spec.rb
@@ -28,6 +28,20 @@ RSpec.describe BookmarkReminderNotificationHandler do
       expect(data["bookmark_name"]).to eq(bookmark.name)
     end
 
+    it "clears the reminder" do
+      subject.send_notification(bookmark)
+      bookmark.reload
+      expect(bookmark.reload.no_reminder?).to eq(true)
+    end
+
+    context "when the delete_when_reminder_sent boolean is true " do
+      it "deletes the bookmark after the reminder gets sent" do
+        bookmark.update(delete_when_reminder_sent: true)
+        subject.send_notification(bookmark)
+        expect(Bookmark.find_by(id: bookmark.id)).to eq(nil)
+      end
+    end
+
     context "when the post has been deleted" do
       it "clears the reminder and does not send a notification" do
         bookmark.post.trash!
diff --git a/test/javascripts/acceptance/bookmarks-test.js b/test/javascripts/acceptance/bookmarks-test.js
index df8fb56e931..762cd1ee071 100644
--- a/test/javascripts/acceptance/bookmarks-test.js
+++ b/test/javascripts/acceptance/bookmarks-test.js
@@ -106,6 +106,30 @@ test("Saving a bookmark with a reminder", async assert => {
   assert.verifySteps(["tomorrow"]);
 });
 
+test("Opening the options panel and remembering the option", async assert => {
+  mockSuccessfulBookmarkPost(assert);
+  await visit("/t/internationalization-localization/280");
+  await openBookmarkModal();
+  await click(".bookmark-options-button");
+  assert.ok(
+    exists(".bookmark-options-panel"),
+    "it should open the options panel"
+  );
+  await click("#delete_when_reminder_sent");
+  await click("#save-bookmark");
+  await openEditBookmarkModal();
+
+  assert.ok(
+    exists(".bookmark-options-panel"),
+    "it should reopen the options panel"
+  );
+  assert.ok(
+    exists(".bookmark-options-panel #delete_when_reminder_sent:checked"),
+    "it should pre-check delete when reminder sent option"
+  );
+  assert.verifySteps(["none"]);
+});
+
 test("Saving a bookmark with no reminder or name", async assert => {
   mockSuccessfulBookmarkPost(assert);
   await visit("/t/internationalization-localization/280");