diff --git a/lib/server/readMetadata.js b/lib/server/readMetadata.js
index 226e2e1a4a..2d7421e261 100644
--- a/lib/server/readMetadata.js
+++ b/lib/server/readMetadata.js
@@ -182,8 +182,15 @@ function processMetadata(file) {
 // process metadata for all docs and save into core/metadata.js
 function generateMetadataDocs() {
   console.log("Generating Metadata for Docs....");
-  const order = readSidebar();
 
+  let order;
+  try {
+    order = readSidebar();
+  } catch (e) {
+    console.error(e);
+    process.exit(1);
+  }
+  
   const regexSubFolder = /translated_docs\/(.*)\/.*/;
 
   const enabledLanguages = [];
@@ -203,6 +210,7 @@ function generateMetadataDocs() {
 
     if (extension === ".md" || extension === ".markdown") {
       const res = processMetadata(file);
+      
       if (!res) {
         return;
       }
diff --git a/lib/server/versionFallback.js b/lib/server/versionFallback.js
index 65a6883571..7abf1a3317 100644
--- a/lib/server/versionFallback.js
+++ b/lib/server/versionFallback.js
@@ -94,6 +94,24 @@ files.forEach(file => {
   const res = extractMetadata(fs.readFileSync(file, "utf8"));
   const metadata = res.metadata;
 
+  if (!metadata.original_id) {
+    console.error(`No 'original_id' field found in ${file}. Perhaps you forgot to add it when importing prior versions of your docs?`);
+    throw new Error(
+      `No 'original_id' field found in ${file}. Perhaps you forgot to add it when importing prior versions of your docs?`
+    );
+  }
+  if (!metadata.id) {
+    console.error(`No 'id' field found in ${file}.`);
+    throw new Error(
+      `No 'id' field found in ${file}.`
+    );
+  } else if (metadata.id.indexOf('version-') === -1) {
+    console.error(`The 'id' field in ${file} is missing the expected 'version-XX-' prefix. Perhaps you forgot to add it when importing prior versions of your docs?`);
+    throw new Error(
+      `The 'id' field in ${file} is missing the expected 'version-XX-' prefix. Perhaps you forgot to add it when importing prior versions of your docs?`
+    );
+  }
+
   if (!(metadata.original_id in available)) {
     available[metadata.original_id] = new Set();
   }
@@ -110,7 +128,7 @@ files.forEach(file => {
 // what the requested version is
 function docVersion(id, req_version) {
   // iterate through versions until a version less than or equal to the requested
-  // is found, then check if that verison has an available file to use
+  // is found, then check if that version has an available file to use
   let requestedFound = false;
   for (let i = 0; i < versions.length; i++) {
     if (versions[i] === req_version) {
@@ -127,7 +145,7 @@ function docVersion(id, req_version) {
     }
   }
   throw new Error(
-    `No document available to use for version ${req_version} of document with id ${id}. Verify that all version files are correct.`
+    `No document with id '${id}' available for use in version ${req_version} of the website. Verify that all version files are correct. Was the document deleted in a past version?`
   );
 }
 
@@ -140,7 +158,13 @@ function diffLatestDoc(file, id) {
 
   const latest = versions[0];
 
-  const version = docVersion(id, latest);
+  let version;
+  try {
+    version = docVersion(id, latest);
+  } catch (e) {
+    console.error(e);
+    process.exit(1);
+  }
   if (!version) {
     return true;
   }
@@ -211,7 +235,13 @@ function docData() {
   languages.filter(language => language.enabled).forEach(language => {
     versions.forEach(version => {
       allIds.forEach(id => {
-        const useVersion = docVersion(id, version);
+        let useVersion;
+        try {
+          useVersion = docVersion(id, version);
+        } catch (e) {
+          console.log(e);
+          process.exit(1);
+        }
         if (!useVersion) {
           return;
         }
@@ -248,7 +278,7 @@ function sidebarVersion(req_version) {
     }
   }
   throw new Error(
-    `No sidebar file available to use for version ${req_version}. Verify that all version files are correct.`
+    `No sidebar file available to use for version ${req_version}. Verify that 'version-${req_version}-sidebars.json' exists.`
   );
 }
 
diff --git a/lib/write-translations.js b/lib/write-translations.js
index 1328be5a55..117501ff02 100755
--- a/lib/write-translations.js
+++ b/lib/write-translations.js
@@ -52,7 +52,13 @@ function execute() {
   files.forEach(file => {
     const extension = path.extname(file);
     if (extension === ".md" || extension === ".markdown") {
-      const res = readMetadata.processMetadata(file);
+      let res;
+      try {
+        res = readMetadata.processMetadata(file);
+      } catch (e) {
+        console.error(e);
+        process.exit(1);
+      }
       if (!res) {
         return;
       }
@@ -84,9 +90,19 @@ function execute() {
   files = glob.sync(CWD + "/versioned_sidebars/*");
   files.forEach(file => {
     if (!file.endsWith("-sidebars.json")) {
+      if (file.endsWith("-sidebar.json")) {
+        console.warn(`Skipping ${file}. Make sure your sidebar filenames follow this format: 'version-VERSION-sidebars.json'.`);        
+      }
       return;
     }
-    sidebarContent = JSON.parse(fs.readFileSync(file, "utf8"));
+    let sidebarContent;
+    try {
+      sidebarContent = JSON.parse(fs.readFileSync(file, "utf8"));
+    } catch (e) {
+      console.error(`Could not parse ${file} into json. ${e}`);
+      process.exit(1);
+    }
+
     Object.keys(sidebarContent).forEach(sb => {
       const categories = sidebarContent[sb];
       Object.keys(categories).forEach(category => {