diff --git a/news/2 Fixes/1194.md b/news/2 Fixes/1194.md
new file mode 100644
index 000000000000..8301b2c8d5dd
--- /dev/null
+++ b/news/2 Fixes/1194.md	
@@ -0,0 +1 @@
+Ensure debugger breaks on `assert` failures.
diff --git a/src/client/debugger/PythonProcessCallbackHandler.ts b/src/client/debugger/PythonProcessCallbackHandler.ts
index 2b18c62ee804..da5d32359577 100644
--- a/src/client/debugger/PythonProcessCallbackHandler.ts
+++ b/src/client/debugger/PythonProcessCallbackHandler.ts
@@ -259,7 +259,7 @@ export class PythonProcessCallbackHandler extends EventEmitter {
             return;
         }
 
-        if (typeName && desc) {
+        if (typeName || desc) {
             let ex: IPythonException = {
                 TypeName: typeName,
                 Description: desc
diff --git a/src/test/debugger/misc.test.ts b/src/test/debugger/misc.test.ts
index 995be0db817a..64efb7f6f405 100644
--- a/src/test/debugger/misc.test.ts
+++ b/src/test/debugger/misc.test.ts
@@ -439,6 +439,42 @@ let testCounter = 0;
             const pauseLocation = { path: path.join(debugFilesPath, 'sample3WithEx.py'), line: 5 };
             await debugClient.assertStoppedLocation('exception', pauseLocation);
         });
+        test('Test pausing on assert failures', async () => {
+            const pauseLocation = { path: path.join(debugFilesPath, 'sampleWithAssertEx.py'), line: 1 };
+
+            function waitToStopDueToException() {
+                return new Promise((resolve, reject) => {
+                    debugClient.once('stopped', (event: DebugProtocol.StoppedEvent) => {
+                        if (event.body.reason === 'exception' &&
+                            event.body.text && event.body.text!.startsWith('AssertionError')) {
+                            resolve();
+                        } else {
+                            reject(new Error('Stopped for some other reason'));
+                        }
+                    });
+                    setTimeout(() => {
+                        reject(new Error(`waitToStopDueToException not received after ${debugClient.defaultTimeout} ms`));
+                    }, debugClient.defaultTimeout);
+                });
+            }
+
+            function setBreakpointFilter(): Promise<any> {
+                if (debuggerType === 'python') {
+                    return Promise.resolve();
+                } else {
+                    return debugClient.waitForEvent('initialized')
+                        .then(() => debugClient.setExceptionBreakpointsRequest({ filters: ['uncaught'] }))
+                        .then(() => debugClient.configurationDoneRequest());
+                }
+            }
+            await Promise.all([
+                debugClient.configurationSequence(),
+                setBreakpointFilter(),
+                debugClient.launch(buildLauncArgs('sampleWithAssertEx.py', false)),
+                waitToStopDueToException(),
+                debugClient.assertStoppedLocation('exception', pauseLocation)
+            ]);
+        });
         test('Test multi-threaded debugging', async function () {
             if (debuggerType !== 'python') {
                 // See GitHub issue #1250
diff --git a/src/test/pythonFiles/debugging/sampleWithAssertEx.py b/src/test/pythonFiles/debugging/sampleWithAssertEx.py
new file mode 100644
index 000000000000..2cfffa40db4b
--- /dev/null
+++ b/src/test/pythonFiles/debugging/sampleWithAssertEx.py
@@ -0,0 +1 @@
+assert False