diff --git a/build/squire-raw.js b/build/squire-raw.js
index cbc6a55..34d1a3a 100644
--- a/build/squire-raw.js
+++ b/build/squire-raw.js
@@ -3102,6 +3102,10 @@ proto._onKey = function ( event ) {
     if ( keyHandlers[ key ] ) {
         keyHandlers[ key ]( this, event, range );
     } else if ( key.length === 1 && !range.collapsed ) {
+        // Record undo checkpoint.
+        this._recordUndoState( range );
+        this._getRangeAndRemoveBookmark( range );
+        // Delete the selection
         deleteContentsOfRange( range );
         this._ensureBottomLine();
         this.setSelection( range );
diff --git a/build/squire.js b/build/squire.js
index af901ce..96bec6d 100644
--- a/build/squire.js
+++ b/build/squire.js
@@ -1,2 +1,2 @@
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r,o;e._recordUndoState(n),Pt(n.startContainer),e._getRangeAndRemoveBookmark(n),r=n.endContainer,o=r.parentNode,n.collapsed&&"A"===o.nodeName&&!r.nextSibling&&n.endOffset===m(r)&&n.setStartAfter(o),e.setSelection(n)},left:function(e){e._removeZWS()},right:function(e){e._removeZWS()}};H&&W&&w.getSelection().modify&&(Yt["meta-left"]=function(e,t){t.preventDefault(),e._sel.modify("move","backward","lineboundary")},Yt["meta-right"]=function(e,t){t.preventDefault(),e._sel.modify("move","forward","lineboundary")}),Yt[Z+"b"]=Gt("B"),Yt[Z+"i"]=Gt("I"),Yt[Z+"u"]=Gt("U"),Yt[Z+"shift-7"]=Gt("S"),Yt[Z+"shift-5"]=Gt("SUB",{tag:"SUP"}),Yt[Z+"shift-6"]=Gt("SUP",{tag:"SUB"}),Yt[Z+"shift-8"]=Qt("makeUnorderedList"),Yt[Z+"shift-9"]=Qt("makeOrderedList"),Yt[Z+"["]=Qt("decreaseQuoteLevel"),Yt[Z+"]"]=Qt("increaseQuoteLevel"),Yt[Z+"y"]=Qt("redo"),Yt[Z+"z"]=Qt("undo"),Yt[Z+"shift-z"]=Qt("redo"),Nt._onKey=function(e){var t=e.keyCode,n=qt[t],r="",o=this.getSelection();n||(n=String.fromCharCode(t).toLowerCase(),/^[A-Za-z0-9]$/.test(n)||(n="")),K&&46===e.which&&(n="."),t>111&&124>t&&(n="f"+(t-111)),"backspace"!==n&&"delete"!==n&&(e.altKey&&(r+="alt-"),e.ctrlKey&&(r+="ctrl-"),e.metaKey&&(r+="meta-")),e.shiftKey&&(r+="shift-"),n=r+n,Yt[n]?Yt[n](this,e,o):1!==n.length||o.collapsed||(this._recordUndoState(o),this._getRangeAndRemoveBookmark(o),at(o),this._ensureBottomLine(),this.setSelection(o),this._updatePath(o,!0))},Nt._getHTML=function(){return this._body.innerHTML},Nt._setHTML=function(e){var t=this._body;t.innerHTML=e;do S(t);while(t=h(t))},Nt.getHTML=function(e){var t,n,r,o,i,a=[];if(e&&(i=this.getSelection())&&this._saveRangeToBookmark(i),q)for(t=this._body;t=h(t);)t.textContent||t.querySelector("BR")||(n=this.createElement("BR"),t.appendChild(n),a.push(n));if(r=this._getHTML().replace(/\u200B/g,""),q)for(o=a.length;o--;)g(a[o]);return i&&this._getRangeAndRemoveBookmark(i),r},Nt.setHTML=function(e){var t,n=this._doc.createDocumentFragment(),r=this.createElement("DIV");r.innerHTML=e,n.appendChild(N(r)),Mt(n,!0),Zt(n),_(n);for(var o=n;o=h(o);)S(o);for(var i=this._body;t=i.lastChild;)i.removeChild(t);i.appendChild(n),S(i),this._undoIndex=-1,this._undoStack.length=0,this._undoStackLength=0,this._isInUndoState=!1;var a=this._getRangeAndRemoveBookmark()||this._createRange(i.firstChild,0);return this._recordUndoState(a),this._getRangeAndRemoveBookmark(a),G?this._lastSelection=a:this.setSelection(a),this._updatePath(a,!0),this},Nt.insertElement=function(e,t){if(t||(t=this.getSelection()),t.collapse(!0),s(e))ot(t,e),t.setStartAfter(e);else{for(var n,r,o=this._body,i=ft(t)||o;i!==o&&!i.nextSibling;)i=i.parentNode;i!==o&&(n=i.parentNode,r=y(n,i.nextSibling,o)),r?(o.insertBefore(e,r),t.setStart(r,0),t.setStart(r,0),lt(t)):(o.appendChild(e),o.appendChild(this.createDefaultBlock()),t.setStart(e,0),t.setEnd(e,0)),this.focus(),this.setSelection(t),this._updatePath(t)
 }return this},Nt.insertImage=function(e){var t=this.createElement("IMG",{src:e});return this.insertElement(t),t};var jt=function(e,t,n){return function(){return this[e](t,n),this.focus()}};Nt.addStyles=function(e){if(e){var t=this._doc.documentElement.firstChild,n=this.createElement("STYLE",{type:"text/css"});n.styleSheet?(t.appendChild(n),n.styleSheet.cssText=e):(n.appendChild(this._doc.createTextNode(e)),t.appendChild(n))}return this},Nt.bold=jt("changeFormat",{tag:"B"}),Nt.italic=jt("changeFormat",{tag:"I"}),Nt.underline=jt("changeFormat",{tag:"U"}),Nt.strikethrough=jt("changeFormat",{tag:"S"}),Nt.subscript=jt("changeFormat",{tag:"SUB"},{tag:"SUP"}),Nt.superscript=jt("changeFormat",{tag:"SUP"},{tag:"SUB"}),Nt.removeBold=jt("changeFormat",null,{tag:"B"}),Nt.removeItalic=jt("changeFormat",null,{tag:"I"}),Nt.removeUnderline=jt("changeFormat",null,{tag:"U"}),Nt.removeStrikethrough=jt("changeFormat",null,{tag:"S"}),Nt.removeSubscript=jt("changeFormat",null,{tag:"SUB"}),Nt.removeSuperscript=jt("changeFormat",null,{tag:"SUP"}),Nt.makeLink=function(e,t){var n=this.getSelection();if(n.collapsed){var r=e.indexOf(":")+1;if(r)for(;"/"===e[r];)r+=1;ot(n,this._doc.createTextNode(e.slice(r)))}return t||(t={}),t.href=e,this.changeFormat({tag:"A",attributes:t},{tag:"A"},n),this.focus()},Nt.removeLink=function(){return this.changeFormat(null,{tag:"A"},this.getSelection(),!0),this.focus()},Nt.setFontFace=function(e){return this.changeFormat({tag:"SPAN",attributes:{"class":"font",style:"font-family: "+e+", sans-serif;"}},{tag:"SPAN",attributes:{"class":"font"}}),this.focus()},Nt.setFontSize=function(e){return this.changeFormat({tag:"SPAN",attributes:{"class":"size",style:"font-size: "+("number"==typeof e?e+"px":e)}},{tag:"SPAN",attributes:{"class":"size"}}),this.focus()},Nt.setTextColour=function(e){return this.changeFormat({tag:"SPAN",attributes:{"class":"colour",style:"color: "+e}},{tag:"SPAN",attributes:{"class":"colour"}}),this.focus()},Nt.setHighlightColour=function(e){return this.changeFormat({tag:"SPAN",attributes:{"class":"highlight",style:"background-color: "+e}},{tag:"SPAN",attributes:{"class":"highlight"}}),this.focus()},Nt.setTextAlignment=function(e){return this.forEachBlock(function(t){t.className=(t.className.split(/\s+/).filter(function(e){return!/align/.test(e)}).join(" ")+" align-"+e).trim(),t.style.textAlign=e},!0),this.focus()},Nt.setTextDirection=function(e){return this.forEachBlock(function(t){t.className=(t.className.split(/\s+/).filter(function(e){return!/dir/.test(e)}).join(" ")+" dir-"+e).trim(),t.dir=e},!0),this.focus()},Nt.increaseQuoteLevel=jt("modifyBlocks",Bt),Nt.decreaseQuoteLevel=jt("modifyBlocks",bt),Nt.makeUnorderedList=jt("modifyBlocks",Lt),Nt.makeOrderedList=jt("modifyBlocks",Rt),Nt.removeList=jt("modifyBlocks",At),Nt.increaseListLevel=jt("modifyBlocks",Ot),Nt.decreaseListLevel=jt("modifyBlocks",Dt),top!==w?(w.editor=new b(e),w.onEditorLoad&&(w.onEditorLoad(w.editor),w.onEditorLoad=null)):w.Squire=b}(document);
\ No newline at end of file
diff --git a/source/Editor.js b/source/Editor.js
index 86009db..891ee53 100644
--- a/source/Editor.js
+++ b/source/Editor.js
@@ -2026,6 +2026,10 @@ proto._onKey = function ( event ) {
     if ( keyHandlers[ key ] ) {
         keyHandlers[ key ]( this, event, range );
     } else if ( key.length === 1 && !range.collapsed ) {
+        // Record undo checkpoint.
+        this._recordUndoState( range );
+        this._getRangeAndRemoveBookmark( range );
+        // Delete the selection
         deleteContentsOfRange( range );
         this._ensureBottomLine();
         this.setSelection( range );