diff --git a/lib/transmit.js b/lib/transmit.js
index 0e9559c5b..be1e7f940 100755
--- a/lib/transmit.js
+++ b/lib/transmit.js
@@ -34,7 +34,15 @@ exports.send = function (request, callback) {
             return internals.fail(request, err, callback);
         }
 
-        return internals.transmit(response, callback);
+        return internals.transmit(response, (err) => {
+
+            if (err) {
+                request._setResponse(err);
+                return internals.fail(request, err, callback);
+            }
+
+            return callback();
+        });
     });
 };
 
@@ -274,23 +282,19 @@ internals.transmit = function (response, callback) {
         response.headers.etag = response.headers.etag.slice(0, -1) + '-' + (response.headers['content-encoding'] || encoding) + '"';
     }
 
-    // Write headers
-
-    const headers = Object.keys(response.headers);
-    for (let i = 0; i < headers.length; ++i) {
-        const header = headers[i];
-        const value = response.headers[header];
-        if (value !== undefined) {
-            request.raw.res.setHeader(header, value);
-        }
-    }
+    // Connection: close
 
     const isInjection = Shot.isInjection(request.raw.req);
     if (!isInjection && !request.connection._started) {
-        request.raw.res.setHeader('connection', 'close');
+        response._header('connection', 'close');
     }
 
-    request.raw.res.writeHead(response.statusCode);
+    // Write headers
+
+    const res = internals.writeHead(response);
+    if (res) {
+        return process.nextTick(callback, res);
+    }
 
     // Write payload
 
@@ -369,6 +373,34 @@ internals.transmit = function (response, callback) {
 };
 
 
+internals.writeHead = function (response) {
+
+    const res = response.request.raw.res;
+
+    try {
+        const headers = Object.keys(response.headers);
+        for (let i = 0; i < headers.length; ++i) {
+            const header = headers[i];
+            const value = response.headers[header];
+            if (value !== undefined) {
+                res.setHeader(header, value);
+            }
+        }
+
+        res.writeHead(response.statusCode);
+    }
+    catch (err) {
+
+        // Reset headers and return err
+
+        res._headers = null;
+        res._headerNames = {};
+
+        return Boom.wrap(err);
+    }
+};
+
+
 internals.Empty = function () {
 
     Stream.Readable.call(this);
diff --git a/test/transmit.js b/test/transmit.js
index e12662570..6945af920 100755
--- a/test/transmit.js
+++ b/test/transmit.js
@@ -2344,6 +2344,55 @@ describe('transmission', () => {
                 done();
             });
         });
+
+        it('returns 500 when node rejects a header', (done) => {
+
+            const server = new Hapi.Server();
+            server.connection();
+
+            const handler = function (request, reply) {
+
+                return reply('ok').header('', 'test');
+            };
+
+            server.route({ method: 'GET', path: '/', handler: handler });
+            server.inject('/', (res) => {
+
+                expect(res.statusCode).to.equal(500);
+                done();
+            });
+        });
+
+        it('returns 500 for out of range status code', (done) => {
+
+            const server = new Hapi.Server();
+            server.connection();
+
+            const handler = function (request, reply) {
+
+                // Patch writeHead to always fail on out of range headers
+
+                const origWriteHead = request.raw.res.writeHead;
+                request.raw.res.writeHead = function (statusCode) {
+
+                    statusCode |= 0;
+                    if (statusCode < 100 || statusCode > 999) {
+                        throw new RangeError(`Invalid status code: ${statusCode}`);
+                    }
+
+                    return origWriteHead.apply(this, arguments);
+                };
+
+                return reply('ok').code(1);
+            };
+
+            server.route({ method: 'GET', path: '/', handler: handler });
+            server.inject('/', (res) => {
+
+                expect(res.statusCode).to.equal(500);
+                done();
+            });
+        });
     });
 
     describe('cache()', () => {