diff --git a/src/RokuDeploy.spec.ts b/src/RokuDeploy.spec.ts
index d93702f..0e0daea 100644
--- a/src/RokuDeploy.spec.ts
+++ b/src/RokuDeploy.spec.ts
@@ -1195,8 +1195,77 @@ describe('index', () => {
             }
             assert.fail('Should not have succeeded');
         });
+
+        it('should throw with HPE_INVALID_CONSTANT and then succeed on retry', async () => {
+            let doPostStub = sinon.stub(rokuDeploy as any, 'doPostRequest');
+            doPostStub.onFirstCall().throws((params) => {
+                throw new ErrorWithCode();
+            });
+            doPostStub.onSecondCall().returns({ body: '..."fileType":"squashfs"...' });
+            try {
+                await rokuDeploy.convertToSquashfs(options);
+            } catch (e) {
+                assert.fail('Should not have throw');
+            }
+        });
+
+        it('should throw and not retry', async () => {
+            let doPostStub = sinon.stub(rokuDeploy as any, 'doPostRequest');
+            doPostStub.onFirstCall().throws((params) => {
+                throw new ErrorWithCode('Something else');
+            });
+            try {
+                await rokuDeploy.convertToSquashfs(options);
+            } catch (e) {
+                expect(e).to.be.instanceof(ErrorWithCode);
+                expect(e['code']).to.be.eql('Something else');
+                return;
+            }
+            assert.fail('Should not have throw');
+        });
+
+        it('should throw with HPE_INVALID_CONSTANT and then fail on retry', async () => {
+            let doPostStub = sinon.stub(rokuDeploy as any, 'doPostRequest');
+            doPostStub.onFirstCall().throws((params) => {
+                throw new ErrorWithCode();
+            });
+            doPostStub.onSecondCall().returns({ body: '..."fileType":"zip"...' });
+            try {
+                await rokuDeploy.convertToSquashfs(options);
+            } catch (e) {
+                expect(e).to.be.instanceof(errors.ConvertError);
+                return;
+            }
+            assert.fail('Should not have throw');
+        });
+
+        it('should fail with HPE_INVALID_CONSTANT and then throw on retry', async () => {
+            let doPostStub = sinon.stub(rokuDeploy as any, 'doPostRequest');
+            doPostStub.onFirstCall().throws((params) => {
+                throw new ErrorWithCode();
+            });
+            doPostStub.onSecondCall().throws((params) => {
+                throw new Error('Never seen');
+            });
+            try {
+                await rokuDeploy.convertToSquashfs(options);
+            } catch (e) {
+                expect(e).to.be.instanceof(ErrorWithCode);
+                return;
+            }
+            assert.fail('Should not have throw');
+        });
     });
 
+    class ErrorWithCode extends Error {
+        code;
+
+        constructor(code = 'HPE_INVALID_CONSTANT') {
+            super();
+            this.code = code;
+        }
+    }
+
     describe('rekeyDevice', () => {
         beforeEach(() => {
             const body = `<device-info>
diff --git a/src/RokuDeploy.ts b/src/RokuDeploy.ts
index 3a04b2e..5468799 100644
--- a/src/RokuDeploy.ts
+++ b/src/RokuDeploy.ts
@@ -507,8 +507,27 @@ export class RokuDeploy {
             archive: '',
             mysubmit: 'Convert to squashfs'
         });
-
-        let results = await this.doPostRequest(requestOptions);
+        let results;
+        try {
+            results = await this.doPostRequest(requestOptions);
+        } catch (error) {
+            //Occasionally this error is seen if the zip size and file name length at the
+            //wrong combination. The device fails to respond to our request with a valid response.
+            //The device successfully converted the zip, so ping the device and and check the response
+            //for "fileType": "squashfs" then return a happy response, otherwise throw the original error
+            if ((error as any).code === 'HPE_INVALID_CONSTANT') {
+                try {
+                    results = await this.doPostRequest(requestOptions, false);
+                    if (/"fileType"\s*:\s*"squashfs"/.test(results.body)) {
+                        return results;
+                    }
+                } catch (e) {
+                    throw error;
+                }
+            } else {
+                throw error;
+            }
+        }
         if (results.body.indexOf('Conversion succeeded') === -1) {
             throw new errors.ConvertError('Squashfs conversion failed');
         }