diff --git a/extensions/notebook/package.json b/extensions/notebook/package.json
index f45984c4a8..eab99a14ff 100644
--- a/extensions/notebook/package.json
+++ b/extensions/notebook/package.json
@@ -336,6 +336,7 @@
 		"error-ex": "^1.3.1",
 		"figures": "^2.0.0",
 		"fs-extra": "^5.0.0",
+		"glob": "^7.1.1",
 		"node-fetch": "^2.3.0",
 		"request": "^2.88.0",
 		"temp-write": "^3.4.0",
@@ -345,6 +346,7 @@
 	"devDependencies": {
 		"@types/decompress": "^4.2.3",
 		"@types/fs-extra": "^5.0.0",
+		"@types/glob": "^7.1.1",
 		"@types/mocha": "^5.2.5",
 		"@types/node": "^11.9.3",
 		"@types/request": "^2.48.1",
diff --git a/extensions/notebook/src/dialog/configurePythonDialog.ts b/extensions/notebook/src/dialog/configurePythonDialog.ts
index d2610f5b5e..3cc505c40d 100644
--- a/extensions/notebook/src/dialog/configurePythonDialog.ts
+++ b/extensions/notebook/src/dialog/configurePythonDialog.ts
@@ -12,6 +12,7 @@ import * as utils from '../common/utils';
 import JupyterServerInstallation from '../jupyter/jupyterServerInstallation';
 import { ApiWrapper } from '../common/apiWrapper';
 import { Deferred } from '../common/promise';
+import { PythonPathLookup, PythonPathInfo } from './pythonPathLookup';
 
 const localize = nls.loadMessageBundle();
 
@@ -21,22 +22,27 @@ export class ConfigurePythonDialog {
 	private readonly DialogTitle = localize('configurePython.dialogName', "Configure Python for Notebooks");
 	private readonly InstallButtonText = localize('configurePython.okButtonText', "Install");
 	private readonly CancelButtonText = localize('configurePython.cancelButtonText', "Cancel");
-	private readonly BrowseButtonText = localize('configurePython.browseButtonText', "Change location");
+	private readonly BrowseButtonText = localize('configurePython.browseButtonText', "Browse");
 	private readonly LocationTextBoxTitle = localize('configurePython.locationTextBoxText', "Python Install Location");
 	private readonly SelectFileLabel = localize('configurePython.selectFileLabel', "Select");
 	private readonly InstallationNote = localize('configurePython.installNote', "This installation will take some time. It is recommended to not close the application until the installation is complete.");
 	private readonly InvalidLocationMsg = localize('configurePython.invalidLocationMsg', "The specified install location is invalid.");
 	private readonly PythonNotFoundMsg = localize('configurePython.pythonNotFoundMsg', "No python installation was found at the specified location.");
 
-	private pythonLocationTextBox: azdata.InputBoxComponent;
+	private pythonLocationDropdown: azdata.DropDownComponent;
+	private pythonDropdownLoader: azdata.LoadingComponent;
 	private browseButton: azdata.ButtonComponent;
 	private newInstallButton: azdata.RadioButtonComponent;
 	private existingInstallButton: azdata.RadioButtonComponent;
 
-	private _setupComplete: Deferred<void>;
+	private setupComplete: Deferred<void>;
+	private pythonPathsPromise: Promise<PythonPathInfo[]>;
+	private usingCustomPath: boolean;
 
 	constructor(private apiWrapper: ApiWrapper, private jupyterInstallation: JupyterServerInstallation) {
-		this._setupComplete = new Deferred<void>();
+		this.setupComplete = new Deferred<void>();
+		this.pythonPathsPromise = (new PythonPathLookup()).getSuggestions();
+		this.usingCustomPath = false;
 	}
 
 	/**
@@ -53,9 +59,9 @@ export class ConfigurePythonDialog {
 		this.dialog.cancelButton.label = this.CancelButtonText;
 		this.dialog.cancelButton.onClick(() => {
 			if (rejectOnCancel) {
-				this._setupComplete.reject(localize('configurePython.pythonInstallDeclined', "Python installation was declined."));
+				this.setupComplete.reject(localize('configurePython.pythonInstallDeclined', "Python installation was declined."));
 			} else {
-				this._setupComplete.resolve();
+				this.setupComplete.resolve();
 			}
 		});
 
@@ -63,21 +69,28 @@ export class ConfigurePythonDialog {
 
 		azdata.window.openDialog(this.dialog);
 
-		return this._setupComplete.promise;
+		return this.setupComplete.promise;
 	}
 
 	private initializeContent(): void {
 		this.dialog.registerContent(async view => {
-			this.pythonLocationTextBox = view.modelBuilder.inputBox()
-				.withProperties<azdata.InputBoxProperties>({
-					value: JupyterServerInstallation.getPythonInstallPath(this.apiWrapper),
+			this.pythonLocationDropdown = view.modelBuilder.dropDown()
+				.withProperties<azdata.DropDownProperties>({
+					value: undefined,
+					values: [],
 					width: '100%'
 				}).component();
+			this.pythonDropdownLoader = view.modelBuilder.loadingComponent()
+				.withItem(this.pythonLocationDropdown)
+				.withProperties<azdata.LoadingComponentProperties>({
+					loading: false
+				})
+				.component();
 
 			this.browseButton = view.modelBuilder.button()
 				.withProperties<azdata.ButtonProperties>({
 					label: this.BrowseButtonText,
-					width: '100px'
+					width: '70px'
 				}).component();
 			this.browseButton.onDidClick(() => this.handleBrowse());
 
@@ -95,7 +108,8 @@ export class ConfigurePythonDialog {
 				}
 			});
 
-			this.createInstallRadioButtons(view.modelBuilder);
+			let useExistingPython = JupyterServerInstallation.getExistingPythonSetting(this.apiWrapper);
+			this.createInstallRadioButtons(view.modelBuilder, useExistingPython);
 
 			let formModel = view.modelBuilder.formContainer()
 				.withFormItems([{
@@ -105,7 +119,7 @@ export class ConfigurePythonDialog {
 					component: this.existingInstallButton,
 					title: ''
 				}, {
-					component: this.pythonLocationTextBox,
+					component: this.pythonDropdownLoader,
 					title: this.LocationTextBoxTitle
 				}, {
 					component: this.browseButton,
@@ -116,11 +130,50 @@ export class ConfigurePythonDialog {
 				}]).component();
 
 			await view.initializeModel(formModel);
+
+			await this.updatePythonPathsDropdown(useExistingPython);
 		});
 	}
 
-	private createInstallRadioButtons(modelBuilder: azdata.ModelBuilder): void {
-		let useExistingPython = JupyterServerInstallation.getExistingPythonSetting(this.apiWrapper);
+	private async updatePythonPathsDropdown(useExistingPython: boolean): Promise<void> {
+		await this.pythonDropdownLoader.updateProperties({ loading: true });
+		try {
+			let pythonPaths: PythonPathInfo[];
+			let dropdownValues: azdata.CategoryValue[];
+			if (useExistingPython) {
+				pythonPaths = await this.pythonPathsPromise;
+				if (pythonPaths && pythonPaths.length > 0) {
+					dropdownValues = pythonPaths.map(path => {
+						return {
+							displayName: `${path.installDir} (Python ${path.version})`,
+							name: path.installDir
+						};
+					});
+				} else {
+					dropdownValues = [{
+						displayName: 'No supported Python versions found.',
+						name: ''
+					}];
+				}
+			} else {
+				let defaultPath = JupyterServerInstallation.DefaultPythonLocation;
+				dropdownValues = [{
+					displayName: `${defaultPath} (Default)`,
+					name: defaultPath
+				}];
+			}
+
+			this.usingCustomPath = false;
+			await this.pythonLocationDropdown.updateProperties({
+				value: dropdownValues[0],
+				values: dropdownValues
+			});
+		} finally {
+			await this.pythonDropdownLoader.updateProperties({ loading: false });
+		}
+	}
+
+	private createInstallRadioButtons(modelBuilder: azdata.ModelBuilder, useExistingPython: boolean): void {
 		let buttonGroup = 'installationType';
 		this.newInstallButton = modelBuilder.radioButton()
 			.withProperties<azdata.RadioButtonProperties>({
@@ -130,6 +183,10 @@ export class ConfigurePythonDialog {
 			}).component();
 		this.newInstallButton.onDidClick(() => {
 			this.existingInstallButton.checked = false;
+			this.updatePythonPathsDropdown(false)
+				.catch(err => {
+					this.showErrorMessage(utils.getErrorMessage(err));
+				});
 		});
 
 		this.existingInstallButton = modelBuilder.radioButton()
@@ -140,11 +197,15 @@ export class ConfigurePythonDialog {
 			}).component();
 		this.existingInstallButton.onDidClick(() => {
 			this.newInstallButton.checked = false;
+			this.updatePythonPathsDropdown(true)
+				.catch(err => {
+					this.showErrorMessage(utils.getErrorMessage(err));
+				});
 		});
 	}
 
 	private async handleInstall(): Promise<boolean> {
-		let pythonLocation = this.pythonLocationTextBox.value;
+		let pythonLocation = (this.pythonLocationDropdown.value as azdata.CategoryValue).name;
 		if (!pythonLocation || pythonLocation.length === 0) {
 			this.showErrorMessage(this.InvalidLocationMsg);
 			return false;
@@ -173,10 +234,10 @@ export class ConfigurePythonDialog {
 		// Don't wait on installation, since there's currently no Cancel functionality
 		this.jupyterInstallation.startInstallProcess(false, { installPath: pythonLocation, existingPython: useExistingPython })
 			.then(() => {
-				this._setupComplete.resolve();
+				this.setupComplete.resolve();
 			})
 			.catch(err => {
-				this._setupComplete.reject(utils.getErrorMessage(err));
+				this.setupComplete.reject(utils.getErrorMessage(err));
 			});
 
 		return true;
@@ -216,7 +277,24 @@ export class ConfigurePythonDialog {
 
 		let fileUris: vscode.Uri[] = await this.apiWrapper.showOpenDialog(options);
 		if (fileUris && fileUris[0]) {
-			this.pythonLocationTextBox.value = fileUris[0].fsPath;
+			let existingValues = <azdata.CategoryValue[]>this.pythonLocationDropdown.values;
+			let filePath = fileUris[0].fsPath;
+			let newValue = {
+				displayName: `${filePath} (Custom)`,
+				name: filePath
+			};
+
+			if (this.usingCustomPath) {
+				existingValues[0] = newValue;
+			} else {
+				existingValues.unshift(newValue);
+				this.usingCustomPath = true;
+			}
+
+			await this.pythonLocationDropdown.updateProperties({
+				value: existingValues[0],
+				values: existingValues
+			});
 		}
 	}
 
diff --git a/extensions/notebook/src/dialog/pythonPathLookup.ts b/extensions/notebook/src/dialog/pythonPathLookup.ts
new file mode 100644
index 0000000000..9c3c6eadee
--- /dev/null
+++ b/extensions/notebook/src/dialog/pythonPathLookup.ts
@@ -0,0 +1,166 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the Source EULA. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as fs from 'fs';
+import * as glob from 'glob';
+
+import * as utils from '../common/utils';
+import * as constants from '../common/constants';
+
+export interface PythonPathInfo {
+	installDir: string;
+	version: string;
+}
+
+export class PythonPathLookup {
+	private condaLocations: string[];
+	constructor() {
+		if (process.platform !== constants.winPlatform) {
+			let userFolder = process.env['HOME'];
+			this.condaLocations = [
+				'/opt/*conda*/bin/python3',
+				'/usr/share/*conda*/bin/python3',
+				`${userFolder}/*conda*/bin/python3`
+			];
+		} else {
+			let userFolder = process.env['USERPROFILE'].replace('\\', '/').replace('C:', '');
+			this.condaLocations = [
+				'/ProgramData/[Mm]iniconda*/python.exe',
+				'/ProgramData/[Aa]naconda*/python.exe',
+				`${userFolder}/[Mm]iniconda*/python.exe`,
+				`${userFolder}/[Aa]naconda*/python.exe`,
+				`${userFolder}/AppData/Local/Continuum/[Mm]iniconda*/python.exe`,
+				`${userFolder}/AppData/Local/Continuum/[Aa]naconda*/python.exe`
+			];
+		}
+	}
+
+	public async getSuggestions(): Promise<PythonPathInfo[]> {
+		let pythonSuggestions = await this.getPythonSuggestions();
+		let condaSuggestions = await this.getCondaSuggestions();
+
+		if (pythonSuggestions) {
+			if (condaSuggestions && condaSuggestions.length > 0) {
+				pythonSuggestions = pythonSuggestions.concat(condaSuggestions);
+			}
+			return this.getInfoForPaths(pythonSuggestions);
+		} else {
+			return [];
+		}
+	}
+
+	private async getCondaSuggestions(): Promise<string[]> {
+		try {
+			let condaResults = await Promise.all(this.condaLocations.map(location => this.globSearch(location)));
+			let condaFiles = condaResults.reduce((first, second) => first.concat(second));
+			return condaFiles.filter(condaPath => condaPath && condaPath.length > 0);
+		} catch (err) {
+		}
+		return [];
+	}
+
+	private globSearch(globPattern: string): Promise<string[]> {
+		return new Promise<string[]>((resolve, reject) => {
+			glob(globPattern, (err, files) => {
+				if (err) {
+					return reject(err);
+				}
+				resolve(Array.isArray(files) ? files : []);
+			});
+		});
+	}
+
+	private async getPythonSuggestions(): Promise<string[]> {
+		let pathsToCheck = this.getPythonCommands();
+
+		let pythonPaths = await Promise.all(pathsToCheck.map(item => this.getPythonPath(item)));
+		let results: string[];
+		if (pythonPaths) {
+			results = pythonPaths.filter(path => path && path.length > 0);
+		} else {
+			results = [];
+		}
+		return results;
+	}
+
+	private async getPythonPath(options: { command: string; args?: string[] }): Promise<string> {
+		try {
+			let args = Array.isArray(options.args) ? options.args : [];
+			args = args.concat(['-c', '"import sys;print(sys.executable)"']);
+			const cmd = `"${options.command}" ${args.join(' ')}`;
+			let output = await utils.executeBufferedCommand(cmd, {});
+			let value = output ? output.trim() : '';
+			if (value.length > 0 && fs.existsSync(value)) {
+				return value;
+			}
+		} catch (err) {
+			// Ignore errors here, since this python version will just be excluded.
+		}
+
+		return undefined;
+	}
+
+	private getPythonCommands(): { command: string; args?: string[] }[] {
+		const paths = ['python3.7', 'python3.6', 'python3', 'python']
+			.map(item => { return { command: item }; });
+		if (process.platform !== constants.winPlatform) {
+			return paths;
+		}
+
+		const versions = ['3.7', '3.6', '3'];
+		return paths.concat(versions.map(version => {
+			return { command: 'py', args: [`-${version}`] };
+		}));
+	}
+
+	private async getInfoForPaths(pythonPaths: string[]): Promise<PythonPathInfo[]> {
+		let pathsInfo = await Promise.all(pythonPaths.map(path => this.getInfoForPath(path)));
+
+		// Remove duplicate paths, and entries with missing values
+		let pathSet = new Set<string>();
+		return pathsInfo.filter(path => {
+			if (!path || !path.installDir || !path.version || path.installDir.length === 0 || path.version.length === 0) {
+				return false;
+			}
+
+			let majorVersion = Number.parseInt(path.version.substring(0, path.version.indexOf('.')));
+			if (Number.isNaN(majorVersion) || majorVersion < 3) {
+				return false;
+			}
+
+			let key = `${path.installDir} ${path.version}`;
+			if (pathSet.has(key)) {
+				return false;
+			} else {
+				pathSet.add(key);
+				return true;
+			}
+		});
+	}
+
+	private async getInfoForPath(pythonPath: string): Promise<PythonPathInfo> {
+		try {
+			// "python --version" returns nothing from executeBufferedCommand with Python 2.X,
+			// so use sys.version_info here instead.
+			let cmd = `"${pythonPath}" -c "import sys;print('.'.join(str(i) for i in sys.version_info[:3]))"`;
+			let output = await utils.executeBufferedCommand(cmd, {});
+			let pythonVersion = output ? output.trim() : '';
+
+			cmd = `"${pythonPath}" -c "import sys;print(sys.exec_prefix)"`;
+			output = await utils.executeBufferedCommand(cmd, {});
+			let pythonPrefix = output ? output.trim() : '';
+
+			if (pythonVersion.length > 0 && pythonPrefix.length > 0) {
+				return {
+					installDir: pythonPrefix,
+					version: pythonVersion
+				};
+			}
+		} catch (err) {
+			// Ignore errors here, since this python version will just be excluded.
+		}
+		return undefined;
+	}
+}
\ No newline at end of file
diff --git a/extensions/notebook/src/jupyter/jupyterServerInstallation.ts b/extensions/notebook/src/jupyter/jupyterServerInstallation.ts
index bd2873b385..2a03800f9d 100644
--- a/extensions/notebook/src/jupyter/jupyterServerInstallation.ts
+++ b/extensions/notebook/src/jupyter/jupyterServerInstallation.ts
@@ -53,7 +53,7 @@ export default class JupyterServerInstallation {
 	private _forceInstall: boolean;
 	private _installInProgress: boolean;
 
-	private static readonly DefaultPythonLocation = path.join(utils.getUserHome(), 'azuredatastudio-python');
+	public static readonly DefaultPythonLocation = path.join(utils.getUserHome(), 'azuredatastudio-python');
 
 	constructor(extensionPath: string, outputChannel: OutputChannel, apiWrapper: ApiWrapper, pythonInstallationPath?: string) {
 		this.extensionPath = extensionPath;
@@ -76,7 +76,12 @@ export default class JupyterServerInstallation {
 			this.outputChannel.appendLine(msgInstallPkgProgress);
 			backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgInstallPkgProgress);
 
-			await this.installPythonPackage(backgroundOperation);
+			try {
+				await this.installPythonPackage(backgroundOperation);
+			} catch (err) {
+				this.outputChannel.appendLine(msgDependenciesInstallationFailed(utils.getErrorMessage(err)));
+				throw err;
+			}
 			this.outputChannel.appendLine(msgPythonDownloadComplete);
 			backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgPythonDownloadComplete);
 
@@ -135,13 +140,13 @@ export default class JupyterServerInstallation {
 			fs.mkdirs(this._pythonInstallationPath, (err) => {
 				if (err) {
 					backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgPythonDirectoryError);
-					reject(err);
+					return reject(err);
 				}
 
 				let totalMegaBytes: number = undefined;
 				let receivedBytes = 0;
 				let printThreshold = 0.1;
-				request.get(pythonDownloadUrl, { timeout: 20000 })
+				let downloadRequest = request.get(pythonDownloadUrl, { timeout: 20000 })
 					.on('error', (downloadError) => {
 						backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgPythonDownloadError);
 						reject(downloadError);
@@ -149,7 +154,7 @@ export default class JupyterServerInstallation {
 					.on('response', (response) => {
 						if (response.statusCode !== 200) {
 							backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgPythonDownloadError);
-							reject(response.statusMessage);
+							return reject(response.statusMessage);
 						}
 
 						let totalBytes = parseInt(response.headers['content-length']);
@@ -166,18 +171,19 @@ export default class JupyterServerInstallation {
 								printThreshold += 0.1;
 							}
 						}
-					})
-					.pipe(fs.createWriteStream(pythonPackagePathLocal))
+					});
+
+				downloadRequest.pipe(fs.createWriteStream(pythonPackagePathLocal))
 					.on('close', () => {
 						//unpack python zip/tar file
 						this.outputChannel.appendLine(msgPythonUnpackPending);
 						let pythonSourcePath = path.join(this._pythonInstallationPath, constants.pythonBundleVersion);
-						if (fs.existsSync(pythonSourcePath)) {
+						if (!this._usingExistingPython && fs.existsSync(pythonSourcePath)) {
 							try {
 								fs.removeSync(pythonSourcePath);
 							} catch (err) {
 								backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgPythonUnpackError);
-								reject(err);
+								return reject(err);
 							}
 						}
 						decompress(pythonPackagePathLocal, this._pythonInstallationPath).then(files => {
@@ -198,6 +204,7 @@ export default class JupyterServerInstallation {
 					.on('error', (downloadError) => {
 						backgroundOperation.updateStatus(azdata.TaskStatus.InProgress, msgPythonDownloadError);
 						reject(downloadError);
+						downloadRequest.abort();
 					});
 			});
 		});
@@ -314,7 +321,6 @@ export default class JupyterServerInstallation {
 						.catch(err => {
 							let errorMsg = msgDependenciesInstallationFailed(utils.getErrorMessage(err));
 							op.updateStatus(azdata.TaskStatus.Failed, errorMsg);
-							this.apiWrapper.showErrorMessage(errorMsg);
 							installReady.reject(errorMsg);
 							this._installInProgress = false;
 						});
diff --git a/extensions/notebook/yarn.lock b/extensions/notebook/yarn.lock
index 784f53bef0..d6990ecd96 100644
--- a/extensions/notebook/yarn.lock
+++ b/extensions/notebook/yarn.lock
@@ -92,6 +92,11 @@
   dependencies:
     "@types/node" "*"
 
+"@types/events@*":
+  version "3.0.0"
+  resolved "https://registry.yarnpkg.com/@types/events/-/events-3.0.0.tgz#2862f3f58a9a7f7c3e78d79f130dd4d71c25c2a7"
+  integrity sha512-EaObqwIvayI5a8dCzhFrjKzVwKLxjoG9T6Ppd5CEo07LRKfQ8Yokw54r5+Wq7FaBQ+yXRvQAYPrHwya1/UFt9g==
+
 "@types/form-data@*":
   version "2.2.1"
   resolved "https://registry.yarnpkg.com/@types/form-data/-/form-data-2.2.1.tgz#ee2b3b8eaa11c0938289953606b745b738c54b1e"
@@ -106,6 +111,20 @@
   dependencies:
     "@types/node" "*"
 
+"@types/glob@^7.1.1":
+  version "7.1.1"
+  resolved "https://registry.yarnpkg.com/@types/glob/-/glob-7.1.1.tgz#aa59a1c6e3fbc421e07ccd31a944c30eba521575"
+  integrity sha512-1Bh06cbWJUHMC97acuD6UMG29nMt0Aqz1vF3guLfG+kHHJhy3AyohZFFxYk2f7Q1SQIrNwvncxAE0N/9s70F2w==
+  dependencies:
+    "@types/events" "*"
+    "@types/minimatch" "*"
+    "@types/node" "*"
+
+"@types/minimatch@*":
+  version "3.0.3"
+  resolved "https://registry.yarnpkg.com/@types/minimatch/-/minimatch-3.0.3.tgz#3dca0e3f33b200fc7d1139c0cd96c1268cadfd9d"
+  integrity sha512-tHq6qdbT9U1IRSGf14CL0pUlULksvY9OZ+5eEgl1N7t+OA3tGvNpxJCzuKQlsNgCVwbAs670L1vcVQi8j9HjnA==
+
 "@types/mocha@^5.2.5":
   version "5.2.6"
   resolved "https://registry.yarnpkg.com/@types/mocha/-/mocha-5.2.6.tgz#b8622d50557dd155e9f2f634b7d68fd38de5e94b"