diff --git a/packages/insomnia/src/main/sentry.ts b/packages/insomnia/src/main/sentry.ts
index 3ff83467625..bbb8d57d26b 100644
--- a/packages/insomnia/src/main/sentry.ts
+++ b/packages/insomnia/src/main/sentry.ts
@@ -4,6 +4,7 @@ import type { SentryRequestType } from '@sentry/types';
 import * as session from '../account/session';
 import { ChangeBufferEvent, database as db } from '../common/database';
 import { SENTRY_OPTIONS } from '../common/sentry';
+import { ExceptionCallback, registerCaptureException } from '../models/capture-exception.util';
 import * as models from '../models/index';
 import { isSettings } from '../models/settings';
 
@@ -44,4 +45,8 @@ export function initializeSentry() {
     ...SENTRY_OPTIONS,
     transport: ElectronSwitchableTransport,
   });
+
+  // this is a hack for logging the sentry error synthetically made for database parent id null issue
+  // currently the database modules are used in the inso-cli as well as it uses NeDB (why?)
+  registerCaptureException(Sentry.captureException as ExceptionCallback);
 }
diff --git a/packages/insomnia/src/models/capture-exception.util.ts b/packages/insomnia/src/models/capture-exception.util.ts
new file mode 100644
index 00000000000..6e0e7f91a7d
--- /dev/null
+++ b/packages/insomnia/src/models/capture-exception.util.ts
@@ -0,0 +1,19 @@
+/**
+ * This is a HACK to work around inso cli using the database module used for Insomnia desktop client.
+ * Now this is getting coupled with Electron side, and CLI should not be really related to the electron at all.
+ * That is another tech debt.
+ */
+export type ExceptionCallback = (exception: unknown, captureContext?: unknown) => string;
+
+let captureException: ExceptionCallback = (exception: unknown) => {
+    console.error(exception);
+    return '';
+};
+
+export function loadCaptureException() {
+    return captureException;
+}
+
+export function registerCaptureException(fn: ExceptionCallback) {
+    captureException = fn;
+}
diff --git a/packages/insomnia/src/models/index.ts b/packages/insomnia/src/models/index.ts
index 387e3a57213..a75ab76a437 100644
--- a/packages/insomnia/src/models/index.ts
+++ b/packages/insomnia/src/models/index.ts
@@ -16,6 +16,7 @@ import {
 import { generateId } from '../common/misc';
 import * as _apiSpec from './api-spec';
 import * as _caCertificate from './ca-certificate';
+import { loadCaptureException } from './capture-exception.util';
 import * as _clientCertificate from './client-certificate';
 import * as _cookieJar from './cookie-jar';
 import * as _environment from './environment';
@@ -163,6 +164,17 @@ export function canDuplicate(type: string) {
   return model ? model.canDuplicate : false;
 }
 
+const assertModelWithParentId = (model: BaseModel, info: string) => {
+  if ((model.type === 'Project' || model.type === 'Workspace') && !model.parentId) {
+    const msg = `[bug] parent id is set null unexpectedly ${model.type} - ${model._id}. ${info}`;
+    console.warn(msg);
+
+    const err = new Error(msg);
+    const capture = loadCaptureException();
+    capture(err);
+  }
+};
+
 export async function initModel<T extends BaseModel>(type: string, ...sources: Record<string, any>[]): Promise<T> {
   const model = getModel(type);
 
@@ -186,6 +198,7 @@ export async function initModel<T extends BaseModel>(type: string, ...sources: R
     model.init(),
   );
   const fullObject = Object.assign({}, objectDefaults, ...sources);
+  assertModelWithParentId(fullObject, 'initModel');
 
   // Generate an _id if there isn't one yet
   if (!fullObject._id) {
@@ -195,7 +208,7 @@ export async function initModel<T extends BaseModel>(type: string, ...sources: R
   // Migrate the model
   // NOTE: Do migration before pruning because we might need to look at those fields
   const migratedDoc = model.migrate(fullObject);
-
+  assertModelWithParentId(migratedDoc, 'model.migrate');
   // Prune extra keys from doc
   for (const key of Object.keys(migratedDoc)) {
     if (!objectDefaults.hasOwnProperty(key)) {
@@ -204,6 +217,8 @@ export async function initModel<T extends BaseModel>(type: string, ...sources: R
     }
   }
 
+  assertModelWithParentId(migratedDoc, 'model.migrate after prune');
+
   // @ts-expect-error -- TSCONVERSION not sure why this error is occurring
   return migratedDoc;
 }
diff --git a/packages/insomnia/src/models/websocket-response.ts b/packages/insomnia/src/models/websocket-response.ts
index c1b6f514776..419899823ad 100644
--- a/packages/insomnia/src/models/websocket-response.ts
+++ b/packages/insomnia/src/models/websocket-response.ts
@@ -60,7 +60,7 @@ export function init(): BaseWebSocketResponse {
   };
 }
 
-export function migrate(doc: Response) {
+export function migrate(doc: WebSocketResponse) {
   return doc;
 }