diff --git a/client/src/components/InlinePanel/index.js b/client/src/components/InlinePanel/index.js
index c450929286..dbb974d0bb 100644
--- a/client/src/components/InlinePanel/index.js
+++ b/client/src/components/InlinePanel/index.js
@@ -181,6 +181,26 @@ export class InlinePanel extends ExpandingFormset {
     return forms.length;
   }
 
+  getFirstchild() {
+    const forms = $('> [data-inline-panel-child]', this.formsElt);
+    return forms.first()[0];
+  }
+
+  isFirstChildEmpty() {
+    let empty = false;
+    const forms = $('> [data-inline-panel-child]', this.formsElt);
+    const title = forms
+      .first()[0]
+      .querySelector('.chosen')
+      .querySelector(`[id$="title"]`);
+    const firsChild = forms.first()[0];
+
+    if (title.textContent === '' && !firsChild.classList.contains('deleted')) {
+      empty = true;
+    }
+    return empty;
+  }
+
   updateAddButtonState() {
     if (this.opts.maxForms) {
       const addButton = $('#' + this.opts.formsetPrefix + '-ADD');
diff --git a/client/src/components/MultipleChooserPanel/index.js b/client/src/components/MultipleChooserPanel/index.js
index 74ca3028fe..6388d5f3c6 100644
--- a/client/src/components/MultipleChooserPanel/index.js
+++ b/client/src/components/MultipleChooserPanel/index.js
@@ -15,10 +15,32 @@ export class MultipleChooserPanel extends InlinePanel {
       `${opts.formsetPrefix}-OPEN_MODAL`,
     );
     openModalButton.addEventListener('click', () => {
+      if (this.isFirstChildEmpty()) {
+        openModalButton.setAttribute(
+          'maxforms-remainder',
+          opts.maxForms + 1 - this.getChildCount(),
+        );
+        openModalButton.setAttribute('maxforms', opts.maxForms);
+      } else {
+        openModalButton.setAttribute(
+          'maxforms-remainder',
+          opts.maxForms - this.getChildCount(),
+        );
+        openModalButton.setAttribute('maxforms', opts.maxForms);
+      }
+
+      if (Number(openModalButton.getAttribute('maxforms-remainder')) === 0) {
+        openModalButton.setAttribute('disabled', 'true');
+      }
+
       this.chooserWidgetFactory.openModal(
         (result) => {
           result.forEach((item) => {
-            if (opts.maxForms && this.getChildCount() >= opts.maxForms) return;
+            if (this.isFirstChildEmpty()) {
+              if (opts.maxForms && this.getChildCount() >= opts.maxForms + 1)
+                return;
+            } else if (opts.maxForms && this.getChildCount() >= opts.maxForms)
+              return;
             this.addForm();
             const formIndex = this.formCount - 1;
             const formPrefix = `${opts.formsetPrefix}-${formIndex}`;
@@ -38,15 +60,30 @@ export class MultipleChooserPanel extends InlinePanel {
       const openModalButton = document.getElementById(
         `${this.opts.formsetPrefix}-OPEN_MODAL`,
       );
-      if (this.getChildCount() >= this.opts.maxForms) {
+      const firstChildButton = this.getFirstchild()
+        .querySelector('.unchosen')
+        .querySelector('button');
+      if (this.isFirstChildEmpty()) {
+        firstChildButton.setAttribute(
+          'maxforms-remainder',
+          this.opts.maxForms + 1 - this.getChildCount(),
+        );
+      }
+      if (
+        this.isFirstChildEmpty()
+          ? this.getChildCount() >= this.opts.maxForms + 1
+          : this.getChildCount() >= this.opts.maxForms
+      ) {
         // need to set the data-force-disabled attribute to override the standard modal-workflow
         // behaviour of re-enabling the button after the modal closes (which potentially happens
         // after this code has run)
         openModalButton.setAttribute('disabled', 'true');
         openModalButton.setAttribute('data-force-disabled', 'true');
+        if (firstChildButton) firstChildButton.setAttribute('disabled', 'true');
       } else {
         openModalButton.removeAttribute('disabled');
         openModalButton.removeAttribute('data-force-disabled');
+        if (firstChildButton) firstChildButton.removeAttribute('disabled');
       }
     }
   }
diff --git a/client/src/includes/chooserModal.js b/client/src/includes/chooserModal.js
index e05a339d0d..863584560a 100644
--- a/client/src/includes/chooserModal.js
+++ b/client/src/includes/chooserModal.js
@@ -218,6 +218,13 @@ class ChooserModalOnloadHandlerFactory {
     }
 
     $(this.chosenLinkSelector, containerElement).on('click', (event) => {
+      const openModalButton = $('[data-multiple-choice-open-modal]')[0];
+
+      if (
+        Number(modal.triggerElement.getAttribute('maxforms-remainder')) === 1
+      ) {
+        openModalButton.setAttribute('disabled', 'true');
+      }
       modal.loadUrl(event.currentTarget.href);
       return false;
     });
@@ -237,9 +244,56 @@ class ChooserModalOnloadHandlerFactory {
   }
 
   updateMultipleChoiceSubmitEnabledState(modal) {
+    const openModalButton = $('[data-multiple-choice-open-modal]')[0];
     // update the enabled state of the multiple choice submit button depending on whether
     // any items have been selected
-    if ($('[data-multiple-choice-select]:checked', modal.body).length) {
+    if (
+      $('[data-multiple-choice-select]:checked', modal.body).length ||
+      $('[data-multiple-choice-select][disabled]', modal.body).length ||
+      (Number(openModalButton.getAttribute('maxforms-remainder')) === 0 &&
+        openModalButton.getAttribute('disabled') === 'false')
+    ) {
+      const messageCounter = document.createElement('p');
+      const selectCount = $(
+        '[data-multiple-choice-select]:checked',
+        modal.body,
+      ).length;
+      messageCounter.textContent = gettext(
+        `${openModalButton.getAttribute('maxforms') - openModalButton.getAttribute('maxforms-remainder') + selectCount}/${openModalButton.getAttribute('maxforms')}`,
+      );
+      messageCounter.style.cssText =
+        'font-weight: bold; font-size: 1rem; padding-top: 15px;';
+
+      const multipleChoice = $('[data-multiple-choice-select]', modal.body);
+      const lastMultipleChoice = multipleChoice.last();
+      const message = lastMultipleChoice.next();
+
+      if (
+        openModalButton.hasAttribute('maxforms') &&
+        Number(openModalButton.getAttribute('maxforms')) !== 1000
+      ) {
+        if (message.length <= 0) {
+          lastMultipleChoice.after(messageCounter);
+        } else {
+          message.remove();
+          lastMultipleChoice.after(messageCounter);
+        }
+      }
+      if (
+        $('[data-multiple-choice-select]:checked', modal.body).length ===
+        Number(openModalButton.getAttribute('maxforms-remainder'))
+      ) {
+        $('[data-multiple-choice-select]:not(:checked)').attr(
+          'disabled',
+          'true',
+        );
+      } else if (
+        $('[data-multiple-choice-select]:checked', modal.body).length <
+        openModalButton.getAttribute('maxforms-remainder')
+      ) {
+        $('[data-multiple-choice-select]', modal.body).removeAttr('disabled');
+      }
+
       $('[data-multiple-choice-submit]', modal.body).removeAttr('disabled');
     } else {
       $('[data-multiple-choice-submit]', modal.body).attr('disabled', true);
diff --git a/wagtail/admin/templates/wagtailadmin/panels/multiple_chooser_panel.html b/wagtail/admin/templates/wagtailadmin/panels/multiple_chooser_panel.html
index 3cc6e945b8..2af8fe7549 100644
--- a/wagtail/admin/templates/wagtailadmin/panels/multiple_chooser_panel.html
+++ b/wagtail/admin/templates/wagtailadmin/panels/multiple_chooser_panel.html
@@ -2,7 +2,7 @@
 {% load i18n l10n wagtailadmin_tags %}
 
 {% block add_button %}
-    <button type="button" class="button button-small button-secondary chooser__choose-button" id="id_{{ self.formset.prefix }}-OPEN_MODAL">
+    <button type="button" data-multiple-choice-open-modal class="button button-small button-secondary chooser__choose-button" id="id_{{ self.formset.prefix }}-OPEN_MODAL">
         {% icon name=icon|default:"plus-inverse" %}{% blocktrans trimmed with label=self.label|lower %}Add {{ label }}{% endblocktrans %}
     </button>
 {% endblock %}