diff --git a/src/sql/workbench/parts/objectExplorer/common/objectExplorerViewTreeShim.ts b/src/sql/workbench/parts/objectExplorer/common/objectExplorerViewTreeShim.ts
index 80a5de4cb3..a558375731 100644
--- a/src/sql/workbench/parts/objectExplorer/common/objectExplorerViewTreeShim.ts
+++ b/src/sql/workbench/parts/objectExplorer/common/objectExplorerViewTreeShim.ts
@@ -16,6 +16,7 @@ import { Disposable } from 'vs/base/common/lifecycle';
 import { generateUuid } from 'vs/base/common/uuid';
 import { createDecorator } from 'vs/platform/instantiation/common/instantiation';
 import { TreeItemCollapsibleState } from 'vs/workbench/common/views';
+import { localize } from 'vs/nls';
 
 export const SERVICE_ID = 'oeShimService';
 export const IOEShimService = createDecorator<IOEShimService>(SERVICE_ID);
@@ -44,45 +45,56 @@ export class OEShimService extends Disposable implements IOEShimService {
 	}
 
 	private async createSession(viewId: string, providerId: string, node: ITreeItem): Promise<string> {
-		let deferred = new Deferred<string>();
 		let connProfile = new ConnectionProfile(this.capabilities, node.payload);
 		connProfile.saveProfile = false;
 		if (this.cm.providerRegistered(providerId)) {
-			await new Promise(async (resolve, reject) => {
-				await this.cm.connect(connProfile, undefined,
-					{ showConnectionDialogOnError: true, showFirewallRuleOnError: true, saveTheConnection: false, showDashboard: false, params: undefined },
-					{
-						onConnectSuccess: async (e, profile) => {
-							let existingConnection = this.cm.findExistingConnection(profile);
-							connProfile = new ConnectionProfile(this.capabilities, await this.cm.addSavedPassword(existingConnection));
-							resolve();
-						},
-						onConnectCanceled: () => {
-							reject('User canceled');
-						},
-						onConnectReject: undefined,
-						onConnectStart: undefined,
-						onDisconnect: undefined
-					});
-			});
+			connProfile = await this.connectOrPrompt(connProfile);
+		} else {
+			// Throw and expect upstream handler to notify about the error
+			// TODO: In the future should use extension recommendations to prompt for correct extension
+			throw new Error(localize('noProviderFound', "Cannot expand as the required connection provider '{0}' was not found", providerId));
 		}
 		let sessionResp = await this.oe.createNewSession(providerId, connProfile);
-		let disp = this.oe.onUpdateObjectExplorerNodes(e => {
-			if (e.connection.id === connProfile.id) {
-				if (e.errorMessage) {
-					deferred.reject();
-					return;
+		let sessionId = sessionResp.sessionId;
+		await new Promise((resolve, reject) => {
+			let listener = this.oe.onUpdateObjectExplorerNodes(e => {
+				if (e.connection.id === connProfile.id) {
+					if (e.errorMessage) {
+						listener.dispose();
+						reject(new Error(e.errorMessage));
+						return;
+					}
+					let rootNode = this.oe.getSession(sessionResp.sessionId).rootNode;
+					// this is how we know it was shimmed
+					if (rootNode.nodePath) {
+						this.nodeHandleMap.set(generateNodeMapKey(viewId, node), rootNode.nodePath);
+					}
 				}
-				let rootNode = this.oe.getSession(sessionResp.sessionId).rootNode;
-				// this is how we know it was shimmed
-				if (rootNode.nodePath) {
-					this.nodeHandleMap.set(generateNodeMapKey(viewId, node), rootNode.nodePath);
-				}
-			}
-			disp.dispose();
-			deferred.resolve(sessionResp.sessionId);
+				listener.dispose();
+				resolve(sessionResp.sessionId);
+			});
 		});
-		return deferred.promise;
+		return sessionId;
+	}
+
+	private async connectOrPrompt(connProfile: ConnectionProfile): Promise<ConnectionProfile> {
+		connProfile = await new Promise(async (resolve, reject) => {
+			await this.cm.connect(connProfile, undefined, { showConnectionDialogOnError: true, showFirewallRuleOnError: true, saveTheConnection: false, showDashboard: false, params: undefined }, {
+				onConnectSuccess: async (e, profile) => {
+					let existingConnection = this.cm.findExistingConnection(profile);
+					connProfile = new ConnectionProfile(this.capabilities, existingConnection);
+					connProfile = <ConnectionProfile>await this.cm.addSavedPassword(connProfile);
+					resolve(connProfile);
+				},
+				onConnectCanceled: () => {
+					reject(new Error(localize('loginCanceled', 'User canceled')));
+				},
+				onConnectReject: undefined,
+				onConnectStart: undefined,
+				onDisconnect: undefined
+			});
+		});
+		return connProfile;
 	}
 
 	public async disconnectNode(viewId: string, node: ITreeItem): Promise<boolean> {