diff --git a/extensions/sql-database-projects/src/dialogs/updateProjectFromDatabaseDialog.ts b/extensions/sql-database-projects/src/dialogs/updateProjectFromDatabaseDialog.ts
index 1d60f0fbc7..a6f7f40375 100644
--- a/extensions/sql-database-projects/src/dialogs/updateProjectFromDatabaseDialog.ts
+++ b/extensions/sql-database-projects/src/dialogs/updateProjectFromDatabaseDialog.ts
@@ -536,6 +536,9 @@ export class UpdateProjectFromDatabaseDialog {
 			connection.password = connection.options.password = credentials.password;
 		}
 
+		const projectFilePath = this.projectFileDropdown!.value! as string;
+		this.project = await Project.openProject(projectFilePath);
+
 		const connectionDetails: azdata.IConnectionProfile = {
 			id: connection.connectionId,
 			userName: connection.userName,
@@ -569,10 +572,10 @@ export class UpdateProjectFromDatabaseDialog {
 
 		const targetEndpointInfo: mssql.SchemaCompareEndpointInfo = {
 			endpointType: mssql.SchemaCompareEndpointType.Project,
-			projectFilePath: this.projectFileDropdown!.value! as string,
+			projectFilePath: projectFilePath,
 			extractTarget: mapExtractTargetEnum(<string>this.folderStructureDropDown!.value),
 			targetScripts: [],
-			dataSchemaProvider: this.project!.getProjectTargetVersion(),
+			dataSchemaProvider: this.project.getProjectTargetVersion(),
 			connectionDetails: connectionDetails,
 			databaseName: '',
 			serverDisplayName: '',
diff --git a/extensions/sql-database-projects/src/test/dialogs/updateProjectFromDatabaseDialog.test.ts b/extensions/sql-database-projects/src/test/dialogs/updateProjectFromDatabaseDialog.test.ts
index 204b3c79d3..ab869a537c 100644
--- a/extensions/sql-database-projects/src/test/dialogs/updateProjectFromDatabaseDialog.test.ts
+++ b/extensions/sql-database-projects/src/test/dialogs/updateProjectFromDatabaseDialog.test.ts
@@ -6,11 +6,14 @@
 import * as azdata from 'azdata';
 import * as should from 'should';
 import * as sinon from 'sinon';
+import * as vscode from 'vscode';
+import * as mssql from 'mssql';
 import * as baselines from '../baselines/baselines';
 import * as testUtils from '../testUtils';
 
 import { UpdateProjectFromDatabaseDialog } from '../../dialogs/updateProjectFromDatabaseDialog';
-import { mockConnectionProfile, mockURIList } from '../testContext';
+import { mockConnectionProfile, mockDatabaseEndpointInfo, mockProjectEndpointInfo, mockURIList } from '../testContext';
+import { UpdateProjectDataModel } from '../../models/api/updateProject';
 
 describe('Update Project From Database Dialog', () => {
 	before(async function (): Promise<void> {
@@ -82,4 +85,59 @@ describe('Update Project From Database Dialog', () => {
 		should.deepEqual(dialog.projectFileDropdown!.values, uriList, `Project file dropdown list should be the sqlproj path (${mockURIList}), but instead was "${dialog.projectFileDropdown!.values}".`);
 		should.equal(dialog.dialog.okButton.enabled, true, 'Okay button should be enabled when dialog is complete.');
 	});
+
+	it('Should populate endpoints correctly when Connection context and workspace with projects is provided', async function (): Promise<void> {
+		sinon.stub(azdata.connection, 'getConnections').resolves([<azdata.connection.ConnectionProfile><unknown>mockConnectionProfile]);
+		sinon.stub(azdata.connection, 'listDatabases').resolves([mockConnectionProfile.databaseName!]);
+
+		const profile = mockConnectionProfile;
+		const dialog = new UpdateProjectFromDatabaseDialog(profile, undefined, mockURIList);
+		await dialog.openDialog();
+		await dialog.populatedInputsPromise;
+
+		let uriList: string[] = [];
+		mockURIList.forEach(projectUri => {
+			uriList.push(projectUri.fsPath as string);
+		});
+
+		should.equal((<any>dialog.serverDropdown!.value).displayName, profile.options['connectionName'], `Server dropdown should be "${profile.options['connectionName']}", but instead was "${(<any>dialog.serverDropdown!.value).displayName}".`);
+		should.equal(dialog.databaseDropdown!.value, profile.databaseName, `Database dropdown should be "${profile.databaseName}", but instead was "${dialog.databaseDropdown!.value}".`);
+		should.equal(dialog.projectFileDropdown!.value, uriList[0], `Project file dropdown should be the first project listed in the workspace URI list (${uriList[0]}), but instead was "${dialog.projectFileDropdown!.value}".`);
+		should.deepEqual(dialog.projectFileDropdown!.values, uriList, `Project file dropdown list should be the workspace URI list (${mockURIList}), but instead was "${dialog.projectFileDropdown!.values}".`);
+		should.equal(dialog.dialog.okButton.enabled, true, 'Okay button should be enabled when dialog is complete.');
+	});
+
+	it('Should successfully complete the handleUpdateButtonClick method call and connect to appropriate call back properties when Connection context and workspace with projects is provided', async function (): Promise<void> {
+		const project = await testUtils.createTestProject(this.test, baselines.openProjectFileBaseline);
+		sinon.stub(azdata.connection, 'getConnections').resolves([<azdata.connection.ConnectionProfile><unknown>mockConnectionProfile]);
+		sinon.stub(azdata.connection, 'listDatabases').resolves([mockConnectionProfile.databaseName!]);
+		sinon.stub(azdata.connection, 'getUriForConnection').resolves('MockUri');
+		sinon.stub(azdata.connection, 'getCredentials').resolves({ ['credentials']: 'credentials' });
+
+		const projectFilePath = project.projectFilePath.toLowerCase();
+		const profile = mockConnectionProfile;
+		mockURIList.unshift(vscode.Uri.file(projectFilePath));
+		const dialog = new UpdateProjectFromDatabaseDialog(profile, undefined, mockURIList);
+		await dialog.openDialog();
+		await dialog.populatedInputsPromise;
+
+		let uriList: string[] = [];
+		mockURIList.forEach(projectUri => {
+			uriList.push(projectUri.fsPath as string);
+		});
+
+		// verify the handleUpdateButtonClick method goes through successfully
+		let model: UpdateProjectDataModel;
+		const testProjectEndpointInfo: mssql.SchemaCompareEndpointInfo = { ...mockProjectEndpointInfo };
+		testProjectEndpointInfo.projectFilePath = projectFilePath;
+		const expectedUpdateProjectDataModel: UpdateProjectDataModel = {
+			sourceEndpointInfo: mockDatabaseEndpointInfo,
+			targetEndpointInfo: testProjectEndpointInfo,
+			action: 0
+		};
+		dialog.updateProjectFromDatabaseCallback = (m) => { model = m; };
+		await dialog.handleUpdateButtonClick();
+
+		should(model!).deepEqual(expectedUpdateProjectDataModel);
+	});
 });
diff --git a/extensions/sql-database-projects/src/test/testContext.ts b/extensions/sql-database-projects/src/test/testContext.ts
index 4777a282aa..5c95d7b637 100644
--- a/extensions/sql-database-projects/src/test/testContext.ts
+++ b/extensions/sql-database-projects/src/test/testContext.ts
@@ -139,3 +139,55 @@ export const mockURIList: vscode.Uri[] = [
 	vscode.Uri.file('/test/folder/folder1/abc1.sqlproj'),
 	vscode.Uri.file('/test/folder/folder2/abc2.sqlproj')
 ];
+
+export const mockConnectionInfo = {
+	id: undefined,
+	userName: 'My User',
+	password: 'My Pwd',
+	serverName: 'My Server',
+	databaseName: 'My Database',
+	connectionName: 'My Connection',
+	providerName: undefined,
+	groupId: 'My GroupId',
+	groupFullName: 'My groupName',
+	authenticationType: azdata.connection.AuthenticationType.SqlLogin,
+	savePassword: false,
+	saveProfile: true,
+	options: {
+		server: 'My Server',
+		database: 'My Database',
+		user: 'My User',
+		password: 'My Pwd',
+		authenticationType: 'SqlLogin',
+		connectionName: 'My Connection Name'
+	}
+};
+
+export const mockProjectEndpointInfo: mssql.SchemaCompareEndpointInfo = {
+	endpointType: mssql.SchemaCompareEndpointType.Project,
+	projectFilePath: '',
+	extractTarget: mssql.ExtractTarget.schemaObjectType,
+	targetScripts: [],
+	dataSchemaProvider: '150',
+	connectionDetails: mockConnectionInfo,
+	databaseName: '',
+	serverDisplayName: '',
+	serverName: '',
+	ownerUri: '',
+	packageFilePath: ''
+};
+
+export const mockDatabaseEndpointInfo: mssql.SchemaCompareEndpointInfo = {
+	endpointType: mssql.SchemaCompareEndpointType.Database,
+	databaseName: 'My Database',
+	serverDisplayName: 'My Connection Name',
+	serverName: 'My Server',
+	connectionDetails: mockConnectionInfo,
+	ownerUri: 'MockUri',
+	projectFilePath: '',
+	extractTarget: mssql.ExtractTarget.schemaObjectType,
+	targetScripts: [],
+	dataSchemaProvider: '',
+	packageFilePath: '',
+	connectionName: 'My Connection Name'
+};