diff --git a/src/addons.js b/src/addons.js
index 4df163d5b..2a9b7b8a2 100644
--- a/src/addons.js
+++ b/src/addons.js
@@ -1125,12 +1125,13 @@ function pipeRequestToFile(url, filename, callback) {
         callback(error);
     });
 
-    writeStream.on('error', done);
+    writeStream.on('error', (error) => done(new BoxError(BoxError.FS_ERROR, `Error writing to ${filename}: ${error.message}`)));
+
     writeStream.on('open', function () {
         // note: do not attach to post callback handler because this will buffer the entire reponse!
         // see https://github.com/request/request/issues/2270
         const req = request.post(url, { rejectUnauthorized: false });
-        req.on('error', done); // network error, dns error, request errored in middle etc
+        req.on('error', (error) => done(new BoxError(BoxError.NETWORK_ERROR, `Request error writing to ${filename}: ${error.message}`))); // network error, dns error, request errored in middle etc
         req.on('response', function (response) {
             if (response.statusCode !== 200) return done(new BoxError(BoxError.ADDONS_ERROR, `Unexpected response code when piping ${url}: ${response.statusCode} message: ${response.statusMessage} filename: ${filename}`));
 
@@ -1171,7 +1172,7 @@ function restoreMySql(app, options, callback) {
         if (error) return callback(error);
 
         var input = fs.createReadStream(dumpPath('mysql', app.id));
-        input.on('error', callback);
+        input.on('error', (error) => callback(new BoxError(BoxError.FS_ERROR, `Error reading input stream when restoring mysql: ${error.message}`)));
 
         const restoreReq = request.post(`https://${result.ip}:3000/` + (options.multipleDatabases ? 'prefixes' : 'databases') + `/${database}/restore?access_token=${result.token}`, { json: true, rejectUnauthorized: false }, function (error, response) {
             if (error) return callback(new BoxError(BoxError.ADDONS_ERROR, `Error restoring mysql: ${error.message}`));
@@ -1353,7 +1354,7 @@ function restorePostgreSql(app, options, callback) {
         if (error) return callback(error);
 
         var input = fs.createReadStream(dumpPath('postgresql', app.id));
-        input.on('error', callback);
+        input.on('error', (error) => callback(new BoxError(BoxError.FS_ERROR, `Error reading input stream when restoring postgresql: ${error.message}`)));
 
         const restoreReq = request.post(`https://${result.ip}:3000/databases/${database}/restore?access_token=${result.token}&username=${username}`, { json: true, rejectUnauthorized: false }, function (error, response) {
             if (error) return callback(new BoxError(BoxError.ADDONS_ERROR, `Error restoring postgresql: ${error.message}`));
@@ -1527,7 +1528,7 @@ function restoreMongoDb(app, options, callback) {
         if (error) return callback(error);
 
         const readStream = fs.createReadStream(dumpPath('mongodb', app.id));
-        readStream.on('error', callback);
+        readStream.on('error', (error) => callback(new BoxError(BoxError.FS_ERROR, `Error reading input stream when restoring mongodb: ${error.message}`)));
 
         const restoreReq = request.post(`https://${result.ip}:3000/databases/${app.id}/restore?access_token=${result.token}`, { json: true, rejectUnauthorized: false }, function (error, response) {
             if (error) return callback(new BoxError(BoxError.ADDONS_ERROR, `Error restoring mongodb: ${error.message}`));
@@ -1700,6 +1701,8 @@ function restoreRedis(app, options, callback) {
 
     debugApp(app, 'Restoring redis');
 
+    callback = once(callback); // protect from multiple returns with streams
+
     getServiceDetails('redis-' + app.id, 'CLOUDRON_REDIS_TOKEN', function (error, result) {
         if (error) return callback(error);
 
@@ -1710,7 +1713,7 @@ function restoreRedis(app, options, callback) {
         } else { // old location of dumps
             input = fs.createReadStream(path.join(paths.APPS_DATA_DIR, app.id, 'redis/dump.rdb'));
         }
-        input.on('error', callback);
+        input.on('error', (error) => callback(new BoxError(BoxError.FS_ERROR, `Error reading input stream when restoring redis: ${error.message}`)));
 
         const restoreReq = request.post(`https://${result.ip}:3000/restore?access_token=${result.token}`, { json: true, rejectUnauthorized: false }, function (error, response) {
             if (error) return callback(new BoxError(BoxError.ADDONS_ERROR, `Error restoring redis: ${error.message}`));
diff --git a/src/apps.js b/src/apps.js
index af25909b1..b04559eb0 100644
--- a/src/apps.js
+++ b/src/apps.js
@@ -1996,7 +1996,7 @@ function uploadFile(appId, sourceFilePath, destFilePath, callback) {
 
     const done = once(function (error) {
         safe.fs.unlinkSync(sourceFilePath); // remove file in /tmp
-        callback(error);
+        callback(new BoxError(BoxError.FS_ERROR, error.message)); // blame it on filesystem for now
     });
 
     // the built-in bash printf understands "%q" but not /usr/bin/printf.
diff --git a/src/boxerror.js b/src/boxerror.js
index 2b4e754f4..34714834e 100644
--- a/src/boxerror.js
+++ b/src/boxerror.js
@@ -88,6 +88,7 @@ BoxError.toHttpError = function (error) {
     case BoxError.FS_ERROR:
     case BoxError.MAIL_ERROR:
     case BoxError.DOCKER_ERROR:
+    case BoxError.ADDONS_ERROR:
         return new HttpError(424, error);
     case BoxError.DATABASE_ERROR:
     case BoxError.INTERNAL_ERROR:
diff --git a/src/mail.js b/src/mail.js
index 11970b701..84140113d 100644
--- a/src/mail.js
+++ b/src/mail.js
@@ -129,7 +129,7 @@ function checkOutboundPort25(callback) {
         relay.status = false;
         relay.value = `Connect to ${smtpServer} failed: ${error.message}. Check if port 25 (outbound) is blocked`;
         client.destroy();
-        callback(error, relay);
+        callback(new BoxError(BoxError.NETWORK_ERROR, `Connect to ${smtpServer} failed.`), relay);
     });
 }
 
diff --git a/src/shell.js b/src/shell.js
index 2f6818c8e..3bb8aa5ae 100644
--- a/src/shell.js
+++ b/src/shell.js
@@ -61,7 +61,7 @@ function spawn(tag, file, args, options, callback) {
         if (code || signal) debug(tag + ' code: %s, signal: %s', code, signal);
         if (code === 0) return callback(null);
 
-        var e = new BoxError(BoxError.SPAWN_ERROR, `${tag} exited with error ${code} signal ${signal}`);
+        let e = new BoxError(BoxError.SPAWN_ERROR, `${tag} exited with code ${code} signal ${signal}`);
         e.code = code;
         e.signal = signal;
         callback(e);
@@ -69,7 +69,8 @@ function spawn(tag, file, args, options, callback) {
 
     cp.on('error', function (error) {
         debug(tag + ' code: %s, signal: %s', error.code, error.signal);
-        callback(error);
+        let e = new BoxError(BoxError.SPAWN_ERROR, `${tag} errored with code ${error.code} message ${error.message}`);
+        callback(e);
     });
 
     return cp;