diff --git a/src/RokuDeploy.spec.ts b/src/RokuDeploy.spec.ts
index a05e50a..b50cd6b 100644
--- a/src/RokuDeploy.spec.ts
+++ b/src/RokuDeploy.spec.ts
@@ -1103,7 +1103,7 @@ describe('index', () => {
             });
         });
 
-        it('rejects when response contains invalid password status code', async () => {
+        it('rejects when response contains update device messaging', async () => {
             options.failOnCompileError = true;
             mockDoPostRequest(`'Failed to check for software update'`, 200);
 
@@ -1117,6 +1117,54 @@ describe('index', () => {
             }
         });
 
+        it('rejects when response contains update device messaging and bad status code on first call', async () => {
+            options.failOnCompileError = true;
+            let spy = sinon.stub(rokuDeploy as any, 'doPostRequest').callsFake((params: any) => {
+                let results: any;
+                if (params?.formData['mysubmit'] === 'Replace') {
+                    results = { response: { statusCode: 500 }, body: `'Failed to check for software update'` };
+                } else {
+                    results = { response: { statusCode: 200 }, body: `` };
+                }
+                rokuDeploy['checkRequest'](results);
+                return Promise.resolve(results);
+            });
+
+            try {
+                await rokuDeploy.publish(options);
+                assert.fail('Should not have succeeded due to roku server compilation failure');
+            } catch (err) {
+                expect(spy.callCount).to.eql(1);
+                expect((err as any).message).to.eql(
+                    errors.UpdateCheckRequiredError.MESSAGE
+                );
+            }
+        });
+
+        it('rejects when response contains update device messaging and bad status code on second call', async () => {
+            options.failOnCompileError = true;
+            let spy = sinon.stub(rokuDeploy as any, 'doPostRequest').callsFake((params: any) => {
+                let results: any;
+                if (params?.formData['mysubmit'] === 'Replace') {
+                    results = { response: { statusCode: 500 }, body: `` };
+                } else {
+                    results = { response: { statusCode: 500 }, body: `'Failed to check for software update'` };
+                }
+                rokuDeploy['checkRequest'](results);
+                return Promise.resolve(results);
+            });
+
+            try {
+                await rokuDeploy.publish(options);
+                assert.fail('Should not have succeeded due to roku server compilation failure');
+            } catch (err) {
+                expect(spy.callCount).to.eql(2);
+                expect((err as any).message).to.eql(
+                    errors.UpdateCheckRequiredError.MESSAGE
+                );
+            }
+        });
+
         it('handles successful deploy', () => {
             options.failOnCompileError = true;
             mockDoPostRequest();
@@ -1208,13 +1256,38 @@ describe('index', () => {
             assert.fail('Should not have succeeded');
         });
 
-        it('Should throw an excpetion', async () => {
+        it('Should throw an exception and call doPost once', async () => {
             options.failOnCompileError = true;
-            mockDoPostRequest('', 577);
+            let spy = mockDoPostRequest('', 577);
 
             try {
                 await rokuDeploy.publish(options);
             } catch (e) {
+                expect(spy.callCount).to.eql(1);
+                assert.ok('Exception was thrown as expected');
+                expect(e).to.be.instanceof(errors.UpdateCheckRequiredError);
+                return;
+            }
+            assert.fail('Should not have succeeded');
+        });
+
+        it('Should throw an exception and should call doPost twice', async () => {
+            options.failOnCompileError = true;
+            let spy = sinon.stub(rokuDeploy as any, 'doPostRequest').callsFake((params: any) => {
+                let results: any;
+                if (params?.formData['mysubmit'] === 'Replace') {
+                    results = { response: { statusCode: 500 }, body: `'not an update error'` };
+                } else {
+                    results = { response: { statusCode: 577 }, body: `` };
+                }
+                rokuDeploy['checkRequest'](results);
+                return Promise.resolve(results);
+            });
+
+            try {
+                await rokuDeploy.publish(options);
+            } catch (e) {
+                expect(spy.callCount).to.eql(2);
                 assert.ok('Exception was thrown as expected');
                 expect(e).to.be.instanceof(errors.UpdateCheckRequiredError);
                 return;
@@ -3698,6 +3771,46 @@ describe('index', () => {
         });
     });
 
+    describe('isUpdateRequiredError', () => {
+        it('returns true if the status code is 577', () => {
+            expect(
+                rokuDeploy['isUpdateRequiredError']({ results: { response: { statusCode: 577 } } })
+            ).to.be.true;
+        });
+
+        it('returns true if the body is an update response from device', () => {
+            const response = `<html>\n<head>\n  <meta charset=\"utf-8\">\n  <meta name=\"HandheldFriendly\" content=\"True\">\n  <title> Roku Development Kit </title>\n\n  <link rel=\"stylesheet\" type=\"text/css\" media=\"screen\" href=\"css/global.css\" />\n</head>\n<body>\n  <div id=\"root\" style=\"background: #fff\">\n\n  </div>\n\n  <script type=\"text/javascript\" src=\"css/global.js\"></script>\n  <script type=\"text/javascript\">\n  \n      // Include core components and resounce bundle (needed)\n      Shell.resource.set(null, {\n          endpoints: {} \n      });\n      Shell.create('Roku.Event.Key');\n      Shell.create('Roku.Events.Resize');\n      Shell.create('Roku.Events.Scroll');  \n      // Create global navigation and render it\n      var nav = Shell.create('Roku.Nav')\n        .trigger('Enable standalone and utility mode - hide user menu, shopping cart, and etc.')\n        .trigger('Use compact footer')\n        .trigger('Hide footer')\n        .trigger('Render', document.getElementById('root'))\n        .trigger('Remove all feature links from header')\n\n      // Retrieve main content body node\n      var node = nav.invoke('Get main body section mounting node');\n      \n      // Create page container and page header\n      var container = Shell.create('Roku.Nav.Page.Standard').trigger('Render', node);\n      node = container.invoke('Get main body node');\n      container.invoke('Get headline node').innerHTML = 'Failed to check for software update';\n\t  // Cannot reach Software Update Server\n      node.innerHTML = '<p>Please make sure that your Roku device is connected to internet and running most recent software.</p> <p> After connecting to internet, go to system settings and check for software update.</p> ';\n\n      var hrDiv = document.createElement('div');\n      hrDiv.innerHTML = '<hr />';\n      node.appendChild(hrDiv);\n\n      var d = document.createElement('div');\n      d.innerHTML = '<br />';\n      node.appendChild(d);\n\n  </script>\n\n\n  <div style=\"display:none\">\n\n  <font color=\"red\">Please make sure that your Roku device is connected to internet, and running most recent software version (d=953108)</font>\n\n  </div>\n\n</body>\n</html>\n`;
+            expect(
+                rokuDeploy['isUpdateRequiredError']({ results: { response: { statusCode: 500 }, body: response } })
+            ).to.be.true;
+        });
+
+        it('returns false on missing results', () => {
+            expect(
+                rokuDeploy['isUpdateRequiredError']({ })
+            ).to.be.false;
+        });
+
+        it('returns false on missing response', () => {
+            expect(
+                rokuDeploy['isUpdateRequiredError']({ results: {} })
+            ).to.be.false;
+        });
+
+        it('returns false on missing status code', () => {
+            expect(
+                rokuDeploy['isUpdateRequiredError']({ results: { response: {} } })
+            ).to.be.false;
+        });
+
+        it('returns false on non-string missing body', () => {
+            expect(
+                rokuDeploy['isUpdateRequiredError']({ results: { response: { statusCode: 500 }, body: false } })
+            ).to.be.false;
+        });
+
+    });
+
     function mockDoGetRequest(body = '', statusCode = 200) {
         return sinon.stub(rokuDeploy as any, 'doGetRequest').callsFake((params) => {
             let results = { response: { statusCode: statusCode }, body: body };
diff --git a/src/RokuDeploy.ts b/src/RokuDeploy.ts
index 6a734dd..26ec742 100644
--- a/src/RokuDeploy.ts
+++ b/src/RokuDeploy.ts
@@ -468,6 +468,8 @@ export class RokuDeploy {
                     //fail if this is a compile error
                     if (this.isCompileError(replaceError.message) && options.failOnCompileError) {
                         throw new errors.CompileError('Compile error', replaceError, replaceError.results);
+                    } else if (this.isUpdateRequiredError(replaceError)) {
+                        throw replaceError;
                     } else {
                         requestOptions.formData.mysubmit = 'Install';
                         response = await this.doPostRequest(requestOptions);
@@ -475,7 +477,7 @@ export class RokuDeploy {
                 }
             } catch (e: any) {
                 //if this is a 577 error, we have high confidence that the device needs to do an update check
-                if (e.results?.response?.statusCode === 577) {
+                if (this.isUpdateRequiredError(e)) {
                     throw new errors.UpdateCheckRequiredError(response, requestOptions, e);
 
                     //a reset connection could be cause by several things, but most likely it's due to the device needing to check for updates
@@ -529,6 +531,13 @@ export class RokuDeploy {
         return !!/["']\s*Failed\s*to\s*check\s*for\s*software\s*update\s*["']/i.exec(responseHtml);
     }
 
+    /**
+     * Checks to see if the exception is due to the device needing to check for updates
+     */
+    private isUpdateRequiredError(e: any): boolean {
+        return e.results?.response?.statusCode === 577 || (typeof e.results?.body === 'string' && this.isUpdateCheckRequiredResponse(e.results.body));
+    }
+
     /**
      * Converts existing loaded package to squashfs for faster loading packages
      * @param options