diff --git a/client/dist/js/TinyMCE_sslink-email.js b/client/dist/js/TinyMCE_sslink-email.js
index c55050900..a495c6cd8 100644
--- a/client/dist/js/TinyMCE_sslink-email.js
+++ b/client/dist/js/TinyMCE_sslink-email.js
@@ -1 +1 @@
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\ No newline at end of file
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\ No newline at end of file
diff --git a/client/dist/js/TinyMCE_sslink-external.js b/client/dist/js/TinyMCE_sslink-external.js
index 20ea77d89..7c0f16367 100644
--- a/client/dist/js/TinyMCE_sslink-external.js
+++ b/client/dist/js/TinyMCE_sslink-external.js
@@ -1 +1 @@
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\ No newline at end of file
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\ No newline at end of file
diff --git a/client/dist/js/TinyMCE_sslink.js b/client/dist/js/TinyMCE_sslink.js
index 6baeba9d9..97c5bde25 100644
--- a/client/dist/js/TinyMCE_sslink.js
+++ b/client/dist/js/TinyMCE_sslink.js
@@ -1 +1 @@
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e=t.Anchor,n=t.Link,o=t.TargetBlank,i=t.Description,r=e&&e.length?"#"+e:"";return r=r.replace(/^#+/,"#"),{href:""+n+r,target:o?"_blank":"",title:i}},insertLinkInEditor:function(t,e){var n=this.getElement().getEditor();n.insertLink(t,null,e),n.addUndo(),n.repaint();var o=n.getInstance(),i=o.selection;setTimeout(function(){return i&&i.collapse()},0)},getOriginalAttributes:function(){var e=this.getElement().getEditor(),n=t(e.getSelectedNode()),o=(n.attr("href")||"").split("#");return{Link:o[0]||"",Anchor:o[1]||"",Description:n.attr("title"),TargetBlank:!!n.attr("target")}}})}),tinymce.PluginManager.add("sslink",function(t){return h.init(t)}),e.default=h},i18n:function(t,e){t.exports=i18n},jquery:function(t,e){t.exports=jQuery},"lib/ShortcodeSerialiser":function(t,e){t.exports=ShortcodeSerialiser},"lib/TinyMCEActionRegistrar":function(t,e){t.exports=TinyMCEActionRegistrar},"react-dom":function(t,e){t.exports=ReactDom}});
\ No newline at end of file
+!function(t){function e(o){if(n[o])return n[o].exports;var i=n[o]={i:o,l:!1,exports:{}};return t[o].call(i.exports,i,i.exports,e),i.l=!0,i.exports}var n={};e.m=t,e.c=n,e.d=function(t,n,o){e.o(t,n)||Object.defineProperty(t,n,{configurable:!1,enumerable:!0,get:o})},e.n=function(t){var n=t&&t.__esModule?function(){return t.default}:function(){return t};return e.d(n,"a",n),n},e.o=function(t,e){return Object.prototype.hasOwnProperty.call(t,e)},e.p="",e(e.s="./client/src/legacy/TinyMCE_sslink.js")}({"./client/src/components/TinymceInlineToolbar/TinymceInlineToolbar.js":function(t,e,n){"use strict";function o(t,e){if(!(t instanceof e))throw new TypeError("Cannot call a class as a function")}function i(t,e,n){var o=Array.isArray(n)?n:[n||""];return!(!t||!e)&&(o=o.map(function(t){return String(t)}).map(function(t){return t.toLowerCase()}),o.filter(function(e){if(e.indexOf("[")>-1&&e.indexOf("]")>-1){var n=e.substring(0,e.indexOf("[")),o=e.substring(e.indexOf("[")+1,e.indexOf("]"));if(n===t.tagName.toLowerCase()&&t.getAttribute(o))return!0}else if(t.tagName&&e===t.tagName.toLowerCase())return!0;return!1}).length>0)}function r(t,e){function n(){i(l,u,o)&&(r.hide(),clearTimeout(c),c=setTimeout(function(){r.show(),r.reposition(l)},300))}var o=arguments.length>2&&void 0!==arguments[2]?arguments[2]:["a"],r=new a(t,e),l=null,c=null,u=!1;return r.hide().renderTo(window.document.body),t.on("remove",function(){r.remove()}),t.on("focus",function(){u=!0}),t.on("blur hide",function(){r.hide(),u=!1}),t.on("nodechange",function(e){var n={element:e.element,parents:e.parents,collapsed:t.selection.isCollapsed()};l=n.selection||n.element,i(l,u,o)?(r.show(),r.reposition(l)):r.hide()}),window.addEventListener("scroll",function(e){e.target.contains(document.querySelector("#"+t.id))&&n()},!0),t.contentDocument.addEventListener("scroll",n),r}Object.defineProperty(e,"__esModule",{value:!0});var l=function(){function t(t,e){for(var n=0;n<e.length;n++){var o=e[n];o.enumerable=o.enumerable||!1,o.configurable=!0,"value"in o&&(o.writable=!0),Object.defineProperty(t,o.key,o)}}return function(e,n,o){return n&&t(e.prototype,n),o&&t(e,o),e}}(),a=function(){function t(e,n){o(this,t),this.mceIframe=document.getElementById(e.id+"_ifr"),this.container=e.getContainer(),this.mceToolbar=null,this.mceStatusbar=null,this.container&&(this.mceToolbar=this.container.querySelector(".mce-toolbar-grp"),this.mceStatusbar=this.container.querySelector(".mce-statusbar")),this.control=tinymce.ui.Factory.create({type:"panel",classes:"inline-toolbar",layout:"stack",items:[{type:"toolbar",items:n}]})}return l(t,[{key:"remove",value:function(){return this.control.remove(),this}},{key:"hide",value:function(){return this.control.hide(),this}},{key:"show",value:function(){return this.control.show(),this}},{key:"renderTo",value:function(t){return this.control.renderTo(t),this}},{key:"setStyles",value:function(t){return tinymce.DOM.setStyles(this.control.getEl(),t),this}},{key:"reposition",value:function(t){if(!t)return this;var e=window.pageXOffset||document.documentElement.scrollLeft,n=window.pageYOffset||document.documentElement.scrollTop,o=window.innerWidth,i=window.innerHeight,r=this.mceIframe?this.mceIframe.getBoundingClientRect():{top:0,right:o,bottom:i,left:0,width:o,height:i},l=this.control.getEl(),a=l.offsetWidth,c=l.offsetHeight,u=t.getBoundingClientRect(),s=(u.left+u.right)/2,d=c+8+5,f=this.mceToolbar?this.mceToolbar.getBoundingClientRect().bottom:0,m=this.mceStatusbar?i-this.mceStatusbar.getBoundingClientRect().top:0,h=Math.max(0,f,r.top),g=Math.max(0,m,i-r.bottom),p=u.top+r.top-h,b=i-r.top-u.bottom-g,k=i-h-g,y="",v=0,T=0;return p>=k||b>=k?this.hide():(this.bottom?b>=d?(y=" mce-arrow-up",v=u.bottom+r.top+n+10):p>=d&&(y=" mce-arrow-down",v=u.top+r.top+n-c-8):p>=d?(y=" mce-arrow-down",v=u.top+r.top+n-c-8):b>=d&&k/2>u.bottom+r.top-h&&(y=" mce-arrow-up",v=u.bottom+r.top+n+10),0===v&&(v=n+h+5),T=s-a/2+r.left+e,u.left<0||u.right>r.width?T=r.left+e+(r.width-a)/2:a>=o?(y+=" mce-arrow-full",T=0):T<0&&u.left+a>o||T+a>o&&u.right-a<0?T=(o-a)/2:T<r.left+e?(y+=" mce-arrow-left",T=u.left+r.left+e):T+a>r.width+r.left+e&&(y+=" mce-arrow-right",T=u.right-a+r.left+e),l.className=l.className.replace(/ ?mce-arrow-[\w]+/g,"")+y,this.setStyles({left:T,top:v}),this)}}]),t}();e.default=a,e.setupTinyMceInlineToolbar=r,e.shouldShowToolbar=i},"./client/src/legacy/TinyMCE_sslink.js":function(t,e,n){"use strict";function o(t){return t&&t.__esModule?t:{default:t}}Object.defineProperty(e,"__esModule",{value:!0});var i=n("lib/TinyMCEActionRegistrar"),r=o(i),l=n("react-dom"),a=o(l),c=n("jquery"),u=o(c),s=n("./client/src/components/TinymceInlineToolbar/TinymceInlineToolbar.js"),d=n("lib/ShortcodeSerialiser"),f=n("i18n"),m=o(f),h={init:function(t){function e(){var e=tinymce.activeEditor.selection.getNode(),n=e.getAttribute("href");n&&t.execCommand(r.default.getEditorCommandFromUrl(n))}var n=this,o=navigator.platform.toUpperCase().includes("MAC")?"⌘":"Ctrl",i=m.default._t("Admin.INSERT_LINK","Insert link"),l=m.default.inject(m.default._t("Admin.INSERT_LINK_WITH_SHORTCUT","Insert link {shortcut}"),{shortcut:"["+o+"+K]"}),a=r.default.getSortedActions("sslink",t.settings.editorIdentifier,!0).map(function(e){return Object.assign({},e,{onclick:function(){return e.onclick(t)}})});t.addButton("sslink",{icon:"link",title:l,type:"menubutton",menu:a}),t.addMenuItem("sslink",{icon:"link",text:i,menu:a}),t.addShortcut("Meta+k","Open link menu",function(){(0,u.default)('[aria-label^="'+i+'"] > button',t.container).first().click()}),t.on("preinit",function(){(0,s.setupTinyMceInlineToolbar)(t,[{type:"button",onClick:e,text:m.default._t("Admin.EDIT_LINK","Edit link")},{type:"button",onClick:function(){return n.handleRemoveLinkClick(t)},text:m.default._t("Admin.REMOVE_LINK","Remove link")}],["a[href]"])})},handleRemoveLinkClick:function(t){var e=t.execCommand("unlink"),n=t.selection.getNode();return n&&void 0!==n.normalize&&n.normalize(),e}};u.default.entwine("ss",function(t){t(".insert-link__dialog-wrapper").entwine({Element:null,Data:{},Bookmark:null,onunmatch:function(){this._clearModal()},_clearModal:function(){a.default.unmountComponentAtNode(this[0])},open:function(){var t=this.getElement().getEditor().getInstance();this.setBookmark(t.selection.getBookmark(2,!0)),this.renderModal(!0)},close:function(){this.setData({}),this.renderModal(!1)},renderModal:function(){},linkCanWrapSelection:function(t){var e=t.getContent()||"",n=t.getNode();if(e)return""!==e.trim();var o=document.createElement(n.nodeName);return o.textContent="Check the outer HTML",!o.outerHTML.includes("Check the outer HTML")&&(n===t.getSel().focusNode&&n===t.getSel().anchorNode&&1===tinymce.activeEditor.dom.createFragment("<a>"+n.outerHTML+"</a>").childNodes.length)},getRequireLinkText:function(){var t=this.getElement().getEditor().getInstance().selection,e=this.linkCanWrapSelection(t);return"A"!==t.getNode().tagName&&!e},handleInsert:function(t){this.getElement().getEditor().getInstance().selection.moveToBookmark(this.getBookmark());var e=this.buildAttributes(t),n=(0,d.createHTMLSanitiser)(),o=n(t.Text);return this.insertLinkInEditor(e,o),this.close(),Promise.resolve()},buildAttributes:function(t){var e=t.Anchor,n=t.Link,o=t.TargetBlank,i=t.Description,r=e&&e.length?"#"+e:"";return r=r.replace(/^#+/,"#"),{href:""+n+r,target:o?"_blank":"",title:i}},insertLinkInEditor:function(t,e){var n=this.getElement().getEditor();n.insertLink(t,null,e),n.addUndo(),n.repaint();var o=n.getInstance(),i=o.selection;setTimeout(function(){return i&&i.collapse()},0)},getOriginalAttributes:function(){var e=this.getElement().getEditor(),n=t(e.getSelectedNode()),o=(n.attr("href")||"").split("#");return{Link:o[0]||"",Anchor:o[1]||"",Description:n.attr("title"),TargetBlank:!!n.attr("target")}}})}),tinymce.PluginManager.add("sslink",function(t){return h.init(t)}),e.default=h},i18n:function(t,e){t.exports=i18n},jquery:function(t,e){t.exports=jQuery},"lib/ShortcodeSerialiser":function(t,e){t.exports=ShortcodeSerialiser},"lib/TinyMCEActionRegistrar":function(t,e){t.exports=TinyMCEActionRegistrar},"react-dom":function(t,e){t.exports=ReactDom}});
\ No newline at end of file
diff --git a/client/src/legacy/TinyMCE_sslink-email.js b/client/src/legacy/TinyMCE_sslink-email.js
index 58e634674..57867fef9 100644
--- a/client/src/legacy/TinyMCE_sslink-email.js
+++ b/client/src/legacy/TinyMCE_sslink-email.js
@@ -59,10 +59,7 @@ jQuery.entwine('ss', ($) => {
       const handleHide = () => this.close();
       const handleInsert = (...args) => this.handleInsert(...args);
       const attrs = this.getOriginalAttributes();
-      const selection = tinymce.activeEditor.selection;
-      const selectionContent = selection.getContent() || '';
-      const tagName = selection.getNode().tagName;
-      const requireLinkText = tagName !== 'A' && selectionContent.trim() === '';
+      const requireLinkText = this.getRequireLinkText();
 
       // create/update the react component
       ReactDOM.render(
diff --git a/client/src/legacy/TinyMCE_sslink-external.js b/client/src/legacy/TinyMCE_sslink-external.js
index 1307fe2a6..4d7d53419 100644
--- a/client/src/legacy/TinyMCE_sslink-external.js
+++ b/client/src/legacy/TinyMCE_sslink-external.js
@@ -54,10 +54,7 @@ jQuery.entwine('ss', ($) => {
       const handleHide = () => this.close();
       const handleInsert = (...args) => this.handleInsert(...args);
       const attrs = this.getOriginalAttributes();
-      const selection = tinymce.activeEditor.selection;
-      const selectionContent = selection.getContent() || '';
-      const tagName = selection.getNode().tagName;
-      const requireLinkText = tagName !== 'A' && selectionContent.trim() === '';
+      const requireLinkText = this.getRequireLinkText();
 
       // create/update the react component
       ReactDOM.render(
diff --git a/client/src/legacy/TinyMCE_sslink.js b/client/src/legacy/TinyMCE_sslink.js
index 01601b46c..e5938d34c 100644
--- a/client/src/legacy/TinyMCE_sslink.js
+++ b/client/src/legacy/TinyMCE_sslink.js
@@ -111,7 +111,53 @@ jQuery.entwine('ss', ($) => {
       /* noop */
     },
 
-  /**
+    /**
+     * @param selection The current tinyMCE selection for this WYSIWYG
+     * @return {Boolean}
+     */
+    linkCanWrapSelection(selection) {
+      const selectionContent = selection.getContent() || '';
+      const node = selection.getNode();
+
+      // If there is direct selected content other than whitespace, we can wrap it.
+      if (selectionContent) {
+        return selectionContent.trim() !== '';
+      }
+
+      // If the selected node type can contain text, and we didn't find selected text above,
+      // then you haven't got a selection we can wrap in a link.
+      const x = document.createElement(node.nodeName);
+      x.textContent = 'Check the outer HTML';
+      if (x.outerHTML.includes('Check the outer HTML')) {
+        return false;
+      }
+
+      // Check if there is a single selected node which can be wrapped in a link.
+      if (node === selection.getSel().focusNode && node === selection.getSel().anchorNode) {
+        const parsed = tinymce.activeEditor.dom.createFragment(`<a>${node.outerHTML}</a>`);
+        if (parsed.childNodes.length === 1) {
+          return true;
+        }
+      }
+
+      return false;
+    },
+
+    /**
+     * Determine whether to show the link text field
+     *
+     * @return {Boolean}
+     */
+    getRequireLinkText() {
+      const selection = this.getElement().getEditor().getInstance().selection;
+      const isValidSelection = this.linkCanWrapSelection(selection);
+      const tagName = selection.getNode().tagName;
+      const requireLinkText = tagName !== 'A' && !isValidSelection;
+
+      return requireLinkText;
+    },
+
+    /**
      * Default behaviour, recommended to overload this and sanitise where needed
      *
      * @param data