diff --git a/components/prism-core.js b/components/prism-core.js
index 4d1c1aefe5..2be3562fb5 100644
--- a/components/prism-core.js
+++ b/components/prism-core.js
@@ -715,12 +715,11 @@ _self.Prism = _;
  * @param {string | TokenStream} content See {@link Token#content content}
  * @param {string|string[]} [alias] The alias(es) of the token.
  * @param {string} [matchedStr=""] A copy of the full string this token was created from.
- * @param {boolean} [greedy=false] Whether the pattern that created this token is greedy or not. Will be removed soon.
  * @class
  * @global
  * @public
  */
-function Token(type, content, alias, matchedStr, greedy) {
+function Token(type, content, alias, matchedStr) {
 	/**
 	 * The type of the token.
 	 *
@@ -748,8 +747,8 @@ function Token(type, content, alias, matchedStr, greedy) {
 	 * @public
 	 */
 	this.alias = alias;
-	this.length = (matchedStr || "").length|0;
-	this.greedy = !!greedy;
+	// Copy of the full string this token was created from
+	this.length = (matchedStr || '').length | 0;
 }
 
 /**
@@ -826,11 +825,15 @@ Token.stringify = function stringify(o, language) {
  * @param {any} grammar
  * @param {LinkedListNode<string | Token>} startNode
  * @param {number} startPos
- * @param {boolean} [oneshot=false]
- * @param {string} [target]
+ * @param {RematchOptions} [rematch]
+ * @returns {void}
  * @private
+ *
+ * @typedef RematchOptions
+ * @property {string} cause
+ * @property {number} reach
  */
-function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, target) {
+function matchGrammar(text, tokenList, grammar, startNode, startPos, rematch) {
 	for (var token in grammar) {
 		if (!grammar.hasOwnProperty(token) || !grammar[token]) {
 			continue;
@@ -840,24 +843,25 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 		patterns = Array.isArray(patterns) ? patterns : [patterns];
 
 		for (var j = 0; j < patterns.length; ++j) {
-			if (target && target == token + ',' + j) {
+			if (rematch && rematch.cause == token + ',' + j) {
 				return;
 			}
 
-			var pattern = patterns[j],
-				inside = pattern.inside,
-				lookbehind = !!pattern.lookbehind,
-				greedy = !!pattern.greedy,
+			var patternObj = patterns[j],
+				inside = patternObj.inside,
+				lookbehind = !!patternObj.lookbehind,
+				greedy = !!patternObj.greedy,
 				lookbehindLength = 0,
-				alias = pattern.alias;
+				alias = patternObj.alias;
 
-			if (greedy && !pattern.pattern.global) {
+			if (greedy && !patternObj.pattern.global) {
 				// Without the global flag, lastIndex won't work
-				var flags = pattern.pattern.toString().match(/[imsuy]*$/)[0];
-				pattern.pattern = RegExp(pattern.pattern.source, flags + 'g');
+				var flags = patternObj.pattern.toString().match(/[imsuy]*$/)[0];
+				patternObj.pattern = RegExp(patternObj.pattern.source, flags + 'g');
 			}
 
-			pattern = pattern.pattern || pattern;
+			/** @type {RegExp} */
+			var pattern = patternObj.pattern || patternObj;
 
 			for ( // iterate the token list and keep track of the current token/string position
 				var currentNode = startNode.next, pos = startPos;
@@ -865,6 +869,10 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 				pos += currentNode.value.length, currentNode = currentNode.next
 			) {
 
+				if (rematch && pos >= rematch.reach) {
+					break;
+				}
+
 				var str = currentNode.value;
 
 				if (tokenList.length > text.length) {
@@ -907,7 +915,7 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 					// find the last node which is affected by this match
 					for (
 						var k = currentNode;
-						k !== tokenList.tail && (p < to || (typeof k.value === 'string' && !k.prev.value.greedy));
+						k !== tokenList.tail && (p < to || typeof k.value === 'string');
 						k = k.next
 					) {
 						removeCount++;
@@ -925,10 +933,6 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 				}
 
 				if (!match) {
-					if (oneshot) {
-						break;
-					}
-
 					continue;
 				}
 
@@ -937,11 +941,16 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 				}
 
 				var from = match.index + lookbehindLength,
-					match = match[0].slice(lookbehindLength),
-					to = from + match.length,
+					matchStr = match[0].slice(lookbehindLength),
+					to = from + matchStr.length,
 					before = str.slice(0, from),
 					after = str.slice(to);
 
+				var reach = pos + str.length;
+				if (rematch && reach > rematch.reach) {
+					rematch.reach = reach;
+				}
+
 				var removeFrom = currentNode.prev;
 
 				if (before) {
@@ -951,19 +960,21 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 
 				removeRange(tokenList, removeFrom, removeCount);
 
-				var wrapped = new Token(token, inside ? _.tokenize(match, inside) : match, alias, match, greedy);
+				var wrapped = new Token(token, inside ? _.tokenize(matchStr, inside) : matchStr, alias, matchStr);
 				currentNode = addAfter(tokenList, removeFrom, wrapped);
 
 				if (after) {
 					addAfter(tokenList, currentNode, after);
 				}
 
-
-				if (removeCount > 1)
-					matchGrammar(text, tokenList, grammar, currentNode.prev, pos, true, token + ',' + j);
-
-				if (oneshot)
-					break;
+				if (removeCount > 1) {
+					// at least one Token object was removed, so we have to do some rematching
+					// this can only happen if the current pattern is greedy
+					matchGrammar(text, tokenList, grammar, currentNode.prev, pos, {
+						cause: token + ',' + j,
+						reach: reach
+					});
+				}
 			}
 		}
 	}
diff --git a/components/prism-core.min.js b/components/prism-core.min.js
index 5ca85cbb43..267167ed8b 100644
--- a/components/prism-core.min.js
+++ b/components/prism-core.min.js
@@ -1 +1 @@
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\ No newline at end of file
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M.hooks.run("before-tokenize",r),r.tokens=M.tokenize(r.code,r.grammar),M.hooks.run("after-tokenize",r),W.stringify(M.util.encode(r.tokens),r.language)},tokenize:function(e,n){var t=n.rest;if(t){for(var r in t)n[r]=t[r];delete n.rest}var a=new i;return I(a,a.head,e),function e(n,t,r,a,i,l){for(var o in r)if(r.hasOwnProperty(o)&&r[o]){var s=r[o];s=Array.isArray(s)?s:[s];for(var u=0;u<s.length;++u){if(l&&l.cause==o+","+u)return;var c=s[u],g=c.inside,f=!!c.lookbehind,h=!!c.greedy,d=0,v=c.alias;if(h&&!c.pattern.global){var p=c.pattern.toString().match(/[imsuy]*$/)[0];c.pattern=RegExp(c.pattern.source,p+"g")}for(var m=c.pattern||c,y=a.next,k=i;y!==t.tail&&!(l&&k>=l.reach);k+=y.value.length,y=y.next){var b=y.value;if(t.length>n.length)return;if(!(b instanceof W)){var x=1;if(h&&y!=t.tail.prev){m.lastIndex=k;var w=m.exec(n);if(!w)break;var A=w.index+(f&&w[1]?w[1].length:0),P=w.index+w[0].length,S=k;for(S+=y.value.length;S<=A;)y=y.next,S+=y.value.length;if(S-=y.value.length,k=S,y.value instanceof W)continue;for(var E=y;E!==t.tail&&(S<P||"string"==typeof E.value);E=E.next)x++,S+=E.value.length;x--,b=n.slice(k,S),w.index-=k}else{m.lastIndex=0;var w=m.exec(b)}if(w){f&&(d=w[1]?w[1].length:0);var A=w.index+d,O=w[0].slice(d),P=A+O.length,L=b.slice(0,A),N=b.slice(P),j=k+b.length;l&&j>l.reach&&(l.reach=j);var C=y.prev;L&&(C=I(t,C,L),k+=L.length),z(t,C,x);var _=new W(o,g?M.tokenize(O,g):O,v,O);y=I(t,C,_),N&&I(t,y,N),1<x&&e(n,t,r,y.prev,k,{cause:o+","+u,reach:j})}}}}}}(e,a,n,a.head,0),function(e){var n=[],t=e.head.next;for(;t!==e.tail;)n.push(t.value),t=t.next;return n}(a)},hooks:{all:{},add:function(e,n){var t=M.hooks.all;t[e]=t[e]||[],t[e].push(n)},run:function(e,n){var t=M.hooks.all[e];if(t&&t.length)for(var r,a=0;r=t[a++];)r(n)}},Token:W};function W(e,n,t,r){this.type=e,this.content=n,this.alias=t,this.length=0|(r||"").length}function i(){var e={value:null,prev:null,next:null},n={value:null,prev:e,next:null};e.next=n,this.head=e,this.tail=n,this.length=0}function I(e,n,t){var r=n.next,a={value:t,prev:n,next:r};return n.next=a,r.prev=a,e.length++,a}function z(e,n,t){for(var r=n.next,a=0;a<t&&r!==e.tail;a++)r=r.next;(n.next=r).prev=n,e.length-=a}if(u.Prism=M,W.stringify=function n(e,t){if("string"==typeof e)return e;if(Array.isArray(e)){var r="";return e.forEach(function(e){r+=n(e,t)}),r}var a={type:e.type,content:n(e.content,t),tag:"span",classes:["token",e.type],attributes:{},language:t},i=e.alias;i&&(Array.isArray(i)?Array.prototype.push.apply(a.classes,i):a.classes.push(i)),M.hooks.run("wrap",a);var l="";for(var o in a.attributes)l+=" "+o+'="'+(a.attributes[o]||"").replace(/"/g,"&quot;")+'"';return"<"+a.tag+' class="'+a.classes.join(" ")+'"'+l+">"+a.content+"</"+a.tag+">"},!u.document)return u.addEventListener&&(M.disableWorkerMessageHandler||u.addEventListener("message",function(e){var n=JSON.parse(e.data),t=n.language,r=n.code,a=n.immediateClose;u.postMessage(M.highlight(r,M.languages[t],t)),a&&u.close()},!1)),M;var e=M.util.currentScript();function t(){M.manual||M.highlightAll()}if(e&&(M.filename=e.src,e.hasAttribute("data-manual")&&(M.manual=!0)),!M.manual){var r=document.readyState;"loading"===r||"interactive"===r&&e&&e.defer?document.addEventListener("DOMContentLoaded",t):window.requestAnimationFrame?window.requestAnimationFrame(t):window.setTimeout(t,16)}return M}(_self);"undefined"!=typeof module&&module.exports&&(module.exports=Prism),"undefined"!=typeof global&&(global.Prism=Prism);
\ No newline at end of file
diff --git a/docs/Token.html b/docs/Token.html
index 08ec3b6c90..44437763fd 100644
--- a/docs/Token.html
+++ b/docs/Token.html
@@ -68,7 +68,7 @@ <h2>
 
     
 
-    <h4 class="name" id="Token"><span class="type-signature"></span>new Token<span class="signature">(type, content, alias<span class="signature-attributes">opt</span>, matchedStr<span class="signature-attributes">opt</span>, greedy<span class="signature-attributes">opt</span>)</span><span class="type-signature"></span></h4>
+    <h4 class="name" id="Token"><span class="type-signature"></span>new Token<span class="signature">(type, content, alias<span class="signature-attributes">opt</span>, matchedStr<span class="signature-attributes">opt</span>)</span><span class="type-signature"></span></h4>
 
     
 
@@ -80,7 +80,7 @@ <h4 class="name" id="Token"><span class="type-signature"></span>new Token<span c
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line723">line 723</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line722">line 722</a>
     </li></ul></dd>
     
 
@@ -311,45 +311,6 @@ <h5>Parameters:</h5>
         </tr>
 
     
-
-        <tr>
-            
-                <td class="name"><code>greedy</code></td>
-            
-
-            <td class="type">
-            
-                
-<span class="param-type">boolean</span>
-
-
-            
-            </td>
-
-            
-                <td class="attributes">
-                
-                    &lt;optional><br>
-                
-
-                
-
-                
-                </td>
-            
-
-            
-                <td class="default">
-                
-                    <code>false</code>
-                
-                </td>
-            
-
-            <td class="description last"><p>Whether the pattern that created this token is greedy or not. Will be removed soon.</p></td>
-        </tr>
-
-    
     </tbody>
 </table>
 
@@ -403,7 +364,7 @@ <h4 class="name" id="alias"><span class="type-signature"></span>alias<span class
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line750">line 750</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line749">line 749</a>
     </li></ul></dd>
     
 
@@ -486,7 +447,7 @@ <h4 class="name" id="content"><span class="type-signature"></span>content<span c
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line742">line 742</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line741">line 741</a>
     </li></ul></dd>
     
 
@@ -563,7 +524,7 @@ <h4 class="name" id="type"><span class="type-signature"></span>type<span class="
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line733">line 733</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line732">line 732</a>
     </li></ul></dd>
     
 
diff --git a/docs/global.html b/docs/global.html
index 04ff438b2b..478976c1a5 100644
--- a/docs/global.html
+++ b/docs/global.html
@@ -143,7 +143,7 @@ <h4 class="name" id="Grammar">Grammar</h4>
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1146">line 1146</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1157">line 1157</a>
     </li></ul></dd>
     
 
@@ -274,7 +274,7 @@ <h4 class="name" id="GrammarToken">GrammarToken</h4>
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1125">line 1125</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1136">line 1136</a>
     </li></ul></dd>
     
 
@@ -559,7 +559,7 @@ <h4 class="name" id="HighlightCallback"><span class="type-signature"></span>High
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1154">line 1154</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1165">line 1165</a>
     </li></ul></dd>
     
 
@@ -713,7 +713,7 @@ <h4 class="name" id="HookCallback"><span class="type-signature"></span>HookCallb
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1164">line 1164</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line1175">line 1175</a>
     </li></ul></dd>
     
 
@@ -859,7 +859,7 @@ <h4 class="name" id="TokenStream">TokenStream</h4>
     
     <dt class="tag-source">Source:</dt>
     <dd class="tag-source"><ul class="dummy"><li>
-        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line755">line 755</a>
+        <a href="prism-core.js.html">prism-core.js</a>, <a href="prism-core.js.html#line754">line 754</a>
     </li></ul></dd>
     
 
diff --git a/docs/prism-core.js.html b/docs/prism-core.js.html
index 4f75eae243..644beffbea 100644
--- a/docs/prism-core.js.html
+++ b/docs/prism-core.js.html
@@ -768,12 +768,11 @@ <h1 class="page-title">prism-core.js</h1>
  * @param {string | TokenStream} content See {@link Token#content content}
  * @param {string|string[]} [alias] The alias(es) of the token.
  * @param {string} [matchedStr=""] A copy of the full string this token was created from.
- * @param {boolean} [greedy=false] Whether the pattern that created this token is greedy or not. Will be removed soon.
  * @class
  * @global
  * @public
  */
-function Token(type, content, alias, matchedStr, greedy) {
+function Token(type, content, alias, matchedStr) {
 	/**
 	 * The type of the token.
 	 *
@@ -801,8 +800,8 @@ <h1 class="page-title">prism-core.js</h1>
 	 * @public
 	 */
 	this.alias = alias;
-	this.length = (matchedStr || "").length|0;
-	this.greedy = !!greedy;
+	// Copy of the full string this token was created from
+	this.length = (matchedStr || '').length | 0;
 }
 
 /**
@@ -879,11 +878,15 @@ <h1 class="page-title">prism-core.js</h1>
  * @param {any} grammar
  * @param {LinkedListNode&lt;string | Token>} startNode
  * @param {number} startPos
- * @param {boolean} [oneshot=false]
- * @param {string} [target]
+ * @param {RematchOptions} [rematch]
+ * @returns {void}
  * @private
+ *
+ * @typedef RematchOptions
+ * @property {string} cause
+ * @property {number} reach
  */
-function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, target) {
+function matchGrammar(text, tokenList, grammar, startNode, startPos, rematch) {
 	for (var token in grammar) {
 		if (!grammar.hasOwnProperty(token) || !grammar[token]) {
 			continue;
@@ -893,24 +896,25 @@ <h1 class="page-title">prism-core.js</h1>
 		patterns = Array.isArray(patterns) ? patterns : [patterns];
 
 		for (var j = 0; j &lt; patterns.length; ++j) {
-			if (target &amp;&amp; target == token + ',' + j) {
+			if (rematch &amp;&amp; rematch.cause == token + ',' + j) {
 				return;
 			}
 
-			var pattern = patterns[j],
-				inside = pattern.inside,
-				lookbehind = !!pattern.lookbehind,
-				greedy = !!pattern.greedy,
+			var patternObj = patterns[j],
+				inside = patternObj.inside,
+				lookbehind = !!patternObj.lookbehind,
+				greedy = !!patternObj.greedy,
 				lookbehindLength = 0,
-				alias = pattern.alias;
+				alias = patternObj.alias;
 
-			if (greedy &amp;&amp; !pattern.pattern.global) {
+			if (greedy &amp;&amp; !patternObj.pattern.global) {
 				// Without the global flag, lastIndex won't work
-				var flags = pattern.pattern.toString().match(/[imsuy]*$/)[0];
-				pattern.pattern = RegExp(pattern.pattern.source, flags + 'g');
+				var flags = patternObj.pattern.toString().match(/[imsuy]*$/)[0];
+				patternObj.pattern = RegExp(patternObj.pattern.source, flags + 'g');
 			}
 
-			pattern = pattern.pattern || pattern;
+			/** @type {RegExp} */
+			var pattern = patternObj.pattern || patternObj;
 
 			for ( // iterate the token list and keep track of the current token/string position
 				var currentNode = startNode.next, pos = startPos;
@@ -918,6 +922,10 @@ <h1 class="page-title">prism-core.js</h1>
 				pos += currentNode.value.length, currentNode = currentNode.next
 			) {
 
+				if (rematch &amp;&amp; pos >= rematch.reach) {
+					break;
+				}
+
 				var str = currentNode.value;
 
 				if (tokenList.length > text.length) {
@@ -960,7 +968,7 @@ <h1 class="page-title">prism-core.js</h1>
 					// find the last node which is affected by this match
 					for (
 						var k = currentNode;
-						k !== tokenList.tail &amp;&amp; (p &lt; to || (typeof k.value === 'string' &amp;&amp; !k.prev.value.greedy));
+						k !== tokenList.tail &amp;&amp; (p &lt; to || typeof k.value === 'string');
 						k = k.next
 					) {
 						removeCount++;
@@ -978,10 +986,6 @@ <h1 class="page-title">prism-core.js</h1>
 				}
 
 				if (!match) {
-					if (oneshot) {
-						break;
-					}
-
 					continue;
 				}
 
@@ -990,11 +994,16 @@ <h1 class="page-title">prism-core.js</h1>
 				}
 
 				var from = match.index + lookbehindLength,
-					match = match[0].slice(lookbehindLength),
-					to = from + match.length,
+					matchStr = match[0].slice(lookbehindLength),
+					to = from + matchStr.length,
 					before = str.slice(0, from),
 					after = str.slice(to);
 
+				var reach = pos + str.length;
+				if (rematch &amp;&amp; reach > rematch.reach) {
+					rematch.reach = reach;
+				}
+
 				var removeFrom = currentNode.prev;
 
 				if (before) {
@@ -1004,19 +1013,21 @@ <h1 class="page-title">prism-core.js</h1>
 
 				removeRange(tokenList, removeFrom, removeCount);
 
-				var wrapped = new Token(token, inside ? _.tokenize(match, inside) : match, alias, match, greedy);
+				var wrapped = new Token(token, inside ? _.tokenize(matchStr, inside) : matchStr, alias, matchStr);
 				currentNode = addAfter(tokenList, removeFrom, wrapped);
 
 				if (after) {
 					addAfter(tokenList, currentNode, after);
 				}
 
-
-				if (removeCount > 1)
-					matchGrammar(text, tokenList, grammar, currentNode.prev, pos, true, token + ',' + j);
-
-				if (oneshot)
-					break;
+				if (removeCount > 1) {
+					// at least one Token object was removed, so we have to do some rematching
+					// this can only happen if the current pattern is greedy
+					matchGrammar(text, tokenList, grammar, currentNode.prev, pos, {
+						cause: token + ',' + j,
+						reach: reach
+					});
+				}
 			}
 		}
 	}
diff --git a/prism.js b/prism.js
index 336152f694..74b8cf894f 100644
--- a/prism.js
+++ b/prism.js
@@ -720,12 +720,11 @@ _self.Prism = _;
  * @param {string | TokenStream} content See {@link Token#content content}
  * @param {string|string[]} [alias] The alias(es) of the token.
  * @param {string} [matchedStr=""] A copy of the full string this token was created from.
- * @param {boolean} [greedy=false] Whether the pattern that created this token is greedy or not. Will be removed soon.
  * @class
  * @global
  * @public
  */
-function Token(type, content, alias, matchedStr, greedy) {
+function Token(type, content, alias, matchedStr) {
 	/**
 	 * The type of the token.
 	 *
@@ -753,8 +752,8 @@ function Token(type, content, alias, matchedStr, greedy) {
 	 * @public
 	 */
 	this.alias = alias;
-	this.length = (matchedStr || "").length|0;
-	this.greedy = !!greedy;
+	// Copy of the full string this token was created from
+	this.length = (matchedStr || '').length | 0;
 }
 
 /**
@@ -831,11 +830,15 @@ Token.stringify = function stringify(o, language) {
  * @param {any} grammar
  * @param {LinkedListNode<string | Token>} startNode
  * @param {number} startPos
- * @param {boolean} [oneshot=false]
- * @param {string} [target]
+ * @param {RematchOptions} [rematch]
+ * @returns {void}
  * @private
+ *
+ * @typedef RematchOptions
+ * @property {string} cause
+ * @property {number} reach
  */
-function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, target) {
+function matchGrammar(text, tokenList, grammar, startNode, startPos, rematch) {
 	for (var token in grammar) {
 		if (!grammar.hasOwnProperty(token) || !grammar[token]) {
 			continue;
@@ -845,24 +848,25 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 		patterns = Array.isArray(patterns) ? patterns : [patterns];
 
 		for (var j = 0; j < patterns.length; ++j) {
-			if (target && target == token + ',' + j) {
+			if (rematch && rematch.cause == token + ',' + j) {
 				return;
 			}
 
-			var pattern = patterns[j],
-				inside = pattern.inside,
-				lookbehind = !!pattern.lookbehind,
-				greedy = !!pattern.greedy,
+			var patternObj = patterns[j],
+				inside = patternObj.inside,
+				lookbehind = !!patternObj.lookbehind,
+				greedy = !!patternObj.greedy,
 				lookbehindLength = 0,
-				alias = pattern.alias;
+				alias = patternObj.alias;
 
-			if (greedy && !pattern.pattern.global) {
+			if (greedy && !patternObj.pattern.global) {
 				// Without the global flag, lastIndex won't work
-				var flags = pattern.pattern.toString().match(/[imsuy]*$/)[0];
-				pattern.pattern = RegExp(pattern.pattern.source, flags + 'g');
+				var flags = patternObj.pattern.toString().match(/[imsuy]*$/)[0];
+				patternObj.pattern = RegExp(patternObj.pattern.source, flags + 'g');
 			}
 
-			pattern = pattern.pattern || pattern;
+			/** @type {RegExp} */
+			var pattern = patternObj.pattern || patternObj;
 
 			for ( // iterate the token list and keep track of the current token/string position
 				var currentNode = startNode.next, pos = startPos;
@@ -870,6 +874,10 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 				pos += currentNode.value.length, currentNode = currentNode.next
 			) {
 
+				if (rematch && pos >= rematch.reach) {
+					break;
+				}
+
 				var str = currentNode.value;
 
 				if (tokenList.length > text.length) {
@@ -912,7 +920,7 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 					// find the last node which is affected by this match
 					for (
 						var k = currentNode;
-						k !== tokenList.tail && (p < to || (typeof k.value === 'string' && !k.prev.value.greedy));
+						k !== tokenList.tail && (p < to || typeof k.value === 'string');
 						k = k.next
 					) {
 						removeCount++;
@@ -930,10 +938,6 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 				}
 
 				if (!match) {
-					if (oneshot) {
-						break;
-					}
-
 					continue;
 				}
 
@@ -942,11 +946,16 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 				}
 
 				var from = match.index + lookbehindLength,
-					match = match[0].slice(lookbehindLength),
-					to = from + match.length,
+					matchStr = match[0].slice(lookbehindLength),
+					to = from + matchStr.length,
 					before = str.slice(0, from),
 					after = str.slice(to);
 
+				var reach = pos + str.length;
+				if (rematch && reach > rematch.reach) {
+					rematch.reach = reach;
+				}
+
 				var removeFrom = currentNode.prev;
 
 				if (before) {
@@ -956,19 +965,21 @@ function matchGrammar(text, tokenList, grammar, startNode, startPos, oneshot, ta
 
 				removeRange(tokenList, removeFrom, removeCount);
 
-				var wrapped = new Token(token, inside ? _.tokenize(match, inside) : match, alias, match, greedy);
+				var wrapped = new Token(token, inside ? _.tokenize(matchStr, inside) : matchStr, alias, matchStr);
 				currentNode = addAfter(tokenList, removeFrom, wrapped);
 
 				if (after) {
 					addAfter(tokenList, currentNode, after);
 				}
 
-
-				if (removeCount > 1)
-					matchGrammar(text, tokenList, grammar, currentNode.prev, pos, true, token + ',' + j);
-
-				if (oneshot)
-					break;
+				if (removeCount > 1) {
+					// at least one Token object was removed, so we have to do some rematching
+					// this can only happen if the current pattern is greedy
+					matchGrammar(text, tokenList, grammar, currentNode.prev, pos, {
+						cause: token + ',' + j,
+						reach: reach
+					});
+				}
 			}
 		}
 	}
diff --git a/tests/core/greedy.js b/tests/core/greedy.js
index ac802b38ad..812828cbff 100644
--- a/tests/core/greedy.js
+++ b/tests/core/greedy.js
@@ -55,8 +55,6 @@ describe('Greedy matching', function () {
 		});
 	});
 
-	// https://github.com/PrismJS/prism/issues/1492
-	/*
 	it('should correctly rematch tokens', function () {
 		testTokens({
 			grammar: {
@@ -75,8 +73,9 @@ describe('Greedy matching', function () {
 			code: `<'> '' ''\n<"> "" ""`,
 			expected: [
 				["c", "<'>"],
-				["a", "''"],
-				["a", "''"],
+				" '",
+				["a", "' '"],
+				"'\n",
 
 				["c", "<\">"],
 				["b", "\"\""],
@@ -84,5 +83,4 @@ describe('Greedy matching', function () {
 			]
 		});
 	});
-	*/
 });