diff --git a/index.js b/index.js
index b8fa563e..193fbc9a 100644
--- a/index.js
+++ b/index.js
@@ -97,12 +97,22 @@ class HtmlWebpackPlugin {
     // Clear the cache once a new HtmlWebpackPlugin is added
     childCompiler.clearCache(compiler);
 
-    // Clear the cache if the child compiler is outdated
+    // Register all HtmlWebpackPlugins instances at the child compiler
     compiler.hooks.thisCompilation.tap('HtmlWebpackPlugin', (compilation) => {
+      // Clear the cache if the child compiler is outdated
       if (childCompiler.hasOutDatedTemplateCache(compilation)) {
         childCompiler.clearCache(compiler);
       }
+      // Add this instances template to the child compiler
       childCompiler.addTemplateToCompiler(compiler, this.options.template);
+      // Add file dependencies of child compiler to parent compiler
+      // to keep them watched even if we get the result from the cache
+      compilation.hooks.additionalChunkAssets.tap('HtmlWebpackPlugin', () => {
+        const childCompilerDependencies = childCompiler.getFileDependencies(compiler);
+        childCompilerDependencies.forEach(fileDependency => {
+          compilation.compilationDependencies.add(fileDependency);
+        });
+      });
     });
 
     // setup hooks for third party plugins
diff --git a/lib/compiler.js b/lib/compiler.js
index 7e431a73..fa099bb2 100644
--- a/lib/compiler.js
+++ b/lib/compiler.js
@@ -36,6 +36,10 @@ class HtmlWebpackChildCompiler {
      * @type {number}
      */
     this.compilationStartedTimestamp;
+    /**
+     * @type {number}
+     */
+    this.compilationEndedTimestamp;
     /**
      * All file dependencies of the child compiler
      * @type {string[]}
@@ -52,23 +56,38 @@ class HtmlWebpackChildCompiler {
    * Add a templatePath to the child compiler
    * The given template will be compiled by `compileTemplates`
    * @param {string} template - The webpack path to the template e.g. `'!!html-loader!index.html'`
+   * @returns {boolean} true if the template is new
    */
   addTemplate (template) {
     const templateId = this.templates.indexOf(template);
     // Don't add the template to the compiler if a similar template was already added
     if (templateId !== -1) {
-      return templateId;
+      return false;
     }
     // A child compiler can compile only once
     // throw an error if a new template is added after the compilation started
-    if (this.compilationPromise) {
+    if (this.isCompiling()) {
       throw new Error('New templates can only be added before `compileTemplates` was called.');
     }
     // Add the template to the childCompiler
-    const newTemplateId = this.templates.length;
     this.templates.push(template);
     // Mark the cache invalid
-    return newTemplateId;
+    return true;
+  }
+
+  /**
+   * Returns true if the childCompiler is currently compiling
+   * @retuns {boolean}
+   */
+  isCompiling () {
+    return !this.didCompile() && this.compilationStartedTimestamp !== undefined;
+  }
+
+  /**
+   * Returns true if the childCOmpiler is done compiling
+   */
+  didCompile () {
+    return this.compilationEndedTimestamp !== undefined;
   }
 
   /**
@@ -158,6 +177,7 @@ class HtmlWebpackChildCompiler {
             entry: entries[entryIndex]
           };
         });
+        this.compilationEndedTimestamp = new Date().getTime();
         resolve(result);
       });
     });
@@ -266,7 +286,12 @@ function getChildCompiler (mainCompiler) {
  * @param {WebpackCompiler} mainCompiler
  */
 function clearCache (mainCompiler) {
-  childCompilerCache.delete(mainCompiler);
+  const childCompiler = getChildCompiler(mainCompiler);
+  // If this childCompiler was already used
+  // remove the entire childCompiler from the cache
+  if (childCompiler.isCompiling() || childCompiler.didCompile()) {
+    childCompilerCache.delete(mainCompiler);
+  }
 }
 
 /**
@@ -275,7 +300,11 @@ function clearCache (mainCompiler) {
  * @param {string} templatePath
  */
 function addTemplateToCompiler (mainCompiler, templatePath) {
-  getChildCompiler(mainCompiler).addTemplate(templatePath);
+  const childCompiler = getChildCompiler(mainCompiler);
+  const isNew = childCompiler.addTemplate(templatePath);
+  if (isNew) {
+    clearCache(mainCompiler);
+  }
 }
 
 /**
@@ -321,9 +350,21 @@ function hasOutDatedTemplateCache (compilation) {
   return childCompiler ? childCompiler.hasOutDatedTemplateCache(compilation) : false;
 }
 
+/**
+ * Return all file dependencies of the last child compilation
+ *
+ * @param {WebpackCompiler} compiler
+ * @returns {Array<string>}
+ */
+function getFileDependencies (compiler) {
+  const childCompiler = getChildCompiler(compiler);
+  return childCompiler.fileDependencies;
+}
+
 module.exports = {
   addTemplateToCompiler,
   compileTemplate,
   hasOutDatedTemplateCache,
-  clearCache
+  clearCache,
+  getFileDependencies
 };