diff --git a/extensions/notebook/src/book/bookTreeView.ts b/extensions/notebook/src/book/bookTreeView.ts
index d3f5f9fd7d..799125adc0 100644
--- a/extensions/notebook/src/book/bookTreeView.ts
+++ b/extensions/notebook/src/book/bookTreeView.ts
@@ -56,6 +56,7 @@ export class BookTreeViewProvider implements vscode.TreeDataProvider<BookTreeIte
 		this.bookTocManager = new BookTocManager();
 		this._bookViewer = vscode.window.createTreeView(this.viewId, { showCollapseAll: true, treeDataProvider: this });
 		this._bookViewer.onDidChangeVisibility(async e => {
+			await this.initialized;
 			// Whenever the viewer changes visibility then try and reveal the currently active document
 			// in the tree view
 			let openDocument = azdata.nb.activeNotebookEditor;
@@ -397,10 +398,10 @@ export class BookTreeViewProvider implements vscode.TreeDataProvider<BookTreeIte
 		if (!uri) {
 			let openDocument = azdata.nb.activeNotebookEditor;
 			if (openDocument) {
-				notebookPath = openDocument.document.uri.fsPath.replace(/\\/g, '/');
+				notebookPath = openDocument.document.uri.fsPath;
 			}
 		} else if (uri.fsPath) {
-			notebookPath = uri.fsPath.replace(/\\/g, '/');
+			notebookPath = uri.fsPath;
 		}
 
 		if (shouldReveal || this._bookViewer?.visible) {
@@ -415,6 +416,7 @@ export class BookTreeViewProvider implements vscode.TreeDataProvider<BookTreeIte
 	}
 
 	async findAndExpandParentNode(notebookPath: string): Promise<BookTreeItem | undefined> {
+		notebookPath = notebookPath.replace(/\\/g, '/');
 		const parentBook = this.books.find(b => notebookPath.indexOf(b.bookPath) > -1);
 		if (!parentBook) {
 			// No parent book, likely because the Notebook is at the top level and not under a Notebook.
@@ -431,23 +433,23 @@ export class BookTreeViewProvider implements vscode.TreeDataProvider<BookTreeIte
 		// the top we'll expand nodes until we find the parent of the Notebook we're looking for
 		// get the children of root node and expand the nodes to the notebook level.
 		await this.getChildren(parentBook.rootNode);
-		// The path to the parent of the Notebook we're looking for (this is the node we're looking to expand)
-		const parentPath = notebookPath.substring(0, notebookPath.lastIndexOf(path.posix.sep));
+		// The path to the Notebook we're looking for (these are the nodes we're looking to expand)
+		const notebookFolders = notebookPath.split('/');
 		// Find number of directories between the Notebook path and the root of the book it's contained in
 		// so we know how many parent nodes to expand
 		let depthOfNotebookInBook: number = path.relative(notebookPath, parentBook.bookPath).split(path.sep).length;
 		// Walk the tree, expanding parent nodes as needed to load the child nodes until
 		// we find the one for our Notebook
-		while (depthOfNotebookInBook > 0) {
+		while (depthOfNotebookInBook > -1) {
 			// check if the notebook is available in already expanded levels.
 			bookItem = parentBook.bookItems.find(b => b.tooltip === notebookPath);
 			if (bookItem) {
 				return bookItem;
 			}
-			// Search for the parent item
-			// notebook can be inside the same folder as parent and can be in a different folder as well
-			// so check for both scenarios.
-			let bookItemToExpand = parentBook.bookItems.find(b => b.tooltip.indexOf(parentPath) > -1) ??
+			// Walk down from the top level parent folder one level at each iteration
+			// and keep expanding until we reach the target notebook leaf
+			let parentBookPath: string = notebookFolders.slice(0, notebookFolders.length - depthOfNotebookInBook).join('/');
+			let bookItemToExpand = parentBook.bookItems.find(b => b.tooltip.indexOf(parentBookPath) > -1) ??
 				parentBook.bookItems.find(b => path.relative(notebookPath, b.tooltip)?.split(path.sep)?.length === depthOfNotebookInBook);
 			if (!bookItemToExpand) {
 				break;
@@ -457,7 +459,13 @@ export class BookTreeViewProvider implements vscode.TreeDataProvider<BookTreeIte
 				// continue expanding and search its children
 				await this.getChildren(bookItemToExpand);
 			}
-			await this._bookViewer.reveal(bookItemToExpand, { select: false, focus: true, expand: 3 });
+			try {
+				// TO DO: Check why the reveal fails during initial load with 'TreeError [bookTreeView] Tree element not found'
+				await this._bookViewer.reveal(bookItemToExpand, { select: false, focus: true, expand: 3 });
+			}
+			catch (e) {
+				console.error(e);
+			}
 			depthOfNotebookInBook--;
 		}
 		return bookItem;
diff --git a/extensions/notebook/src/book/bookTrustManager.ts b/extensions/notebook/src/book/bookTrustManager.ts
index 8ecb5b90f9..2348343dfc 100644
--- a/extensions/notebook/src/book/bookTrustManager.ts
+++ b/extensions/notebook/src/book/bookTrustManager.ts
@@ -29,7 +29,7 @@ export class BookTrustManager implements IBookTrustManager {
 		let hasTrustedBookPath: boolean = treeBookItems
 			.filter(bookItem => trustableBookPaths.some(trustableBookPath => trustableBookPath === path.join(bookItem.book.root, path.sep)))
 			.some(bookItem => normalizedNotebookUri.startsWith(bookItem.book.version === BookVersion.v1 ? path.join(bookItem.book.root, 'content', path.sep) : path.join(bookItem.book.root, path.sep)));
-		let isNotebookTrusted = hasTrustedBookPath && this.books.some(bookModel => bookModel.getNotebook(normalizedNotebookUri));
+		let isNotebookTrusted = hasTrustedBookPath && this.books.some(bookModel => bookModel.getNotebook(vscode.Uri.file(normalizedNotebookUri).fsPath));
 		return isNotebookTrusted;
 	}
 
diff --git a/extensions/notebook/src/test/book/book.test.ts b/extensions/notebook/src/test/book/book.test.ts
index 3e6ae6e2e8..42422606b3 100644
--- a/extensions/notebook/src/test/book/book.test.ts
+++ b/extensions/notebook/src/test/book/book.test.ts
@@ -233,7 +233,7 @@ describe('BooksTreeViewTests', function () {
 
 			});
 
-			it.skip('getParent should return when element is a valid child notebook', async () => {
+			it('getParent should return when element is a valid child notebook', async () => {
 				let parent = await bookTreeViewProvider.getParent();
 				should(parent).be.undefined();
 
@@ -243,8 +243,9 @@ describe('BooksTreeViewTests', function () {
 			});
 
 			it('revealActiveDocumentInViewlet should return correct bookItem for highlight', async () => {
-				let notebook1Path = vscode.Uri.file(path.join(rootFolderPath, 'Book', 'content', 'notebook1.ipynb')).fsPath;
+				let notebook1Path = path.join(rootFolderPath, 'Book', 'content', 'notebook1.ipynb').replace(/\\/g, '/');
 				let currentSelection = await bookTreeViewProvider.findAndExpandParentNode(notebook1Path);
+				should(currentSelection).not.be.undefined();
 				equalBookItems(currentSelection, expectedNotebook1);
 			});
 
@@ -327,8 +328,9 @@ describe('BooksTreeViewTests', function () {
 			});
 
 			it('revealActiveDocumentInViewlet should return correct bookItem for highlight', async () => {
-				let notebook1Path = path.join(rootFolderPath, 'Book', 'content', 'notebook1.ipynb');
+				let notebook1Path = path.join(rootFolderPath, 'Book', 'content', 'notebook1.ipynb').replace(/\\/g, '/');
 				let currentSelection = await providedbookTreeViewProvider.findAndExpandParentNode(notebook1Path);
+				should(currentSelection).not.be.undefined();
 				equalBookItems(currentSelection, expectedNotebook1);
 			});