The Flask Mega-Tutorial Part X: Email Support

This is the tenth installment of the Flask Mega-Tutorial series, in which I'm going to tell you how your application can send emails to your users, and how to build a password recovery feature on top of the email support.

For your reference, below is a list of the articles in this series.

Note 1: If you are looking for the legacy version of this tutorial, it's here.

Note 2: If you would like to support my work on this blog, or just don't have patience to wait for weekly articles, I am offering the complete version of this tutorial packaged as an ebook or a set of videos. For more information, visit courses.miguelgrinberg.com.

The application is doing pretty well on the database front now, so in this chapter I want to depart from that topic and add another important piece that most web applications need, which is the sending of emails.

Why does an application need to email its users? There are many reasons, but one common one is to solve authentication related problems. In this chapter I'm going to add a password reset feature for users that forget their password. When a user requests a password reset, the application will send an email with a specially crafted link. The user then needs to click that link to have access to a form in which to set a new password.

The GitHub links for this chapter are: Browse, Zip, Diff.

Introduction to Flask-Mail

As far as the actual sending of emails, Flask has a popular extension called Flask-Mail that can make the task very easy. As always, this extension is installed with pip:

(venv) $ pip install flask-mail

The password reset links will have a secure token in them. To generate these tokens, I'm going to use JSON Web Tokens, which also have a popular Python package:

(venv) $ pip install pyjwt

The Flask-Mail extension is configured from the app.config object. Remember when in Chapter 7 I added the email configuration for sending yourself an email whenever an error occurred in production? I did not tell you this then, but my choice of configuration variables was modeled after Flask-Mail's requirements, so there isn't really any additional work that is needed, the configuration variables are already in the application.

Like most Flask extensions, you need to create an instance right after the Flask application is created. In this case this is an object of class Mail:

app/__init__.py: Flask-Mail instance.

# ...
from flask_mail import Mail

app = Flask(__name__)
# ...
mail = Mail(app)

If you are planning to test sending of emails you have the same two options I mentioned in Chapter 7. If you want to use an emulated email server, Python provides one that is very handy that you can start in a second terminal with the following command:

(venv) $ python -m smtpd -n -c DebuggingServer localhost:8025

To configure for this server you will need to set two environment variables:

(venv) $ export MAIL_SERVER=localhost
(venv) $ export MAIL_PORT=8025

If you prefer to have emails sent for real, you need to use a real email server. If you have one, then you just need to set the MAIL_SERVER, MAIL_PORT, MAIL_USE_TLS, MAIL_USERNAME and MAIL_PASSWORD environment variables for it. If you want a quick solution, you can use a Gmail account to send email, with the following settings:

(venv) $ export MAIL_SERVER=smtp.googlemail.com
(venv) $ export MAIL_PORT=587
(venv) $ export MAIL_USE_TLS=1
(venv) $ export MAIL_USERNAME=<your-gmail-username>
(venv) $ export MAIL_PASSWORD=<your-gmail-password>

If you are using Microsoft Windows, you need to replace export with set in each of the export statements above.

Remember that the security features in your Gmail account may prevent the application from sending emails through it unless you explicitly allow "less secure apps" access to your Gmail account. You can read about this here, and if you are concerned about the security of your account, you can create a secondary account that you configure just for testing emails, or you can enable less secure apps only temporarily to run your tests and then revert back to the more secure default.

Flask-Mail Usage

To learn how Flask-Mail works, I'll show you how to send an email from a Python shell. So fire up Python with flask shell, and then run the following commands:

>>> from flask_mail import Message
>>> from app import mail
>>> msg = Message('test subject', sender=app.config['ADMINS'][0],
... recipients=['your-email@example.com'])
>>> msg.body = 'text body'
>>> msg.html = '<h1>HTML body</h1>'
>>> mail.send(msg)

The snippet of code above will send an email to a list of email addresses that you put in the recipients argument. I put the sender as the first configured admin (I've added the ADMINS configuration variable in Chapter 7). The email will have plain text and HTML versions, so depending on how your email client is configured you may see one or the other.

So as you see, this is pretty simple. Now let's integrate emails into the application.

A Simple Email Framework

I will begin by writing a helper function that sends an email, which is basically a generic version of the shell exercise from the previous section. I will put this function in a new module called app/email.py:

app/email.py: Email sending wrapper function.

from flask_mail import Message
from app import mail

def send_email(subject, sender, recipients, text_body, html_body):
    msg = Message(subject, sender=sender, recipients=recipients)
    msg.body = text_body
    msg.html = html_body

Flask-Mail supports some features that I'm not utilizing here such as Cc and Bcc lists. Be sure to check the Flask-Mail Documentation if you are interested in those options.

Requesting a Password Reset

As I mentioned above, I want users to have the option to request their password to be reset. For this purpose I'm going to add a link in the login page:

app/templates/login.html: Password reset link in login form.

        Forgot Your Password?
        <a href="{{ url_for('reset_password_request') }}">Click to Reset It</a>

When the user clicks the link, a new web form will appear that requests the user's email address as a way to initiate the password reset process. Here is the form class:

app/forms.py: Reset password request form.

class ResetPasswordRequestForm(FlaskForm):
    email = StringField('Email', validators=[DataRequired(), Email()])
    submit = SubmitField('Request Password Reset')

And here is the corresponding HTML template:

app/templates/reset_password_request.html: Reset password request template.

{% extends "base.html" %}

{% block content %}
    <h1>Reset Password</h1>
    <form action="" method="post">
        {{ form.hidden_tag() }}
            {{ form.email.label }}<br>
            {{ form.email(size=64) }}<br>
            {% for error in form.email.errors %}
            <span style="color: red;">[{{ error }}]</span>
            {% endfor %}
        <p>{{ form.submit() }}</p>
{% endblock %}

I also need a view function to handle this form:

app/routes.py: Reset password request view function.

from app.forms import ResetPasswordRequestForm
from app.email import send_password_reset_email

@app.route('/reset_password_request', methods=['GET', 'POST'])
def reset_password_request():
    if current_user.is_authenticated:
        return redirect(url_for('index'))
    form = ResetPasswordRequestForm()
    if form.validate_on_submit():
        user = User.query.filter_by(email=form.email.data).first()
        if user:
        flash('Check your email for the instructions to reset your password')
        return redirect(url_for('login'))
    return render_template('reset_password_request.html',
                           title='Reset Password', form=form)

This view function is fairly similar to others that process a form. I start by making sure the user is not logged in. If the user is logged in, then there is no point in using the password reset functionality, so I redirect to the index page.

When the form is submitted and valid, I look up the user by the email provided by the user in the form. If I find the user, I send a password reset email. I'm using a send_password_reset_email() helper function to do this. I will show you this function below.

After the email is sent, I flash a message directing the user to look for the email for further instructions, and then redirect back to the login page. You may notice that the flashed message is displayed even if the email provided by the user is unknown. This is so that clients cannot use this form to figure out if a given user is a member or not.

Password Reset Tokens

Before I implement the send_password_reset_email() function, I need to have a way to generate a password request link. This is going to be the link that is sent to the user via email. When the link is clicked, a page where a new password can be set is presented to the user. The tricky part of this plan is to make sure that only valid reset links can be used to reset an account's password.

The links are going to be provisioned with a token, and this token will be validated before allowing the password change, as proof that the user that requested the email has access to the email address on the account. A very popular token standard for this type of process is the JSON Web Token, or JWT. The nice thing about JWTs is that they are self contained. You can send a token to a user in an email, and when the user clicks the link that feeds the token back into the application, it can be verified on its own.

How do JWTs work? Nothing better than a quick Python shell session to understand them:

>>> import jwt
>>> token = jwt.encode({'a': 'b'}, 'my-secret', algorithm='HS256')
>>> token
>>> jwt.decode(token, 'my-secret', algorithms=['HS256'])
{'a': 'b'}

The {'a': 'b'} dictionary is an example payload that is going to be written into the token. To make the token secure, a secret key needs to be provided to be used in creating a cryptographic signature. For this example I have used the string 'my-secret', but with the application I'm going to use the SECRET_KEY from the configuration. The algorithm argument specifies how the token is to be generated. The HS256 algorithm is the most widely used.

As you can see the resulting token is a long sequence of characters. But do not think that this is an encrypted token. The contents of the token, including the payload, can be decoded easily by anyone (don't believe me? Copy the above token and then enter it in the JWT debugger to see its contents). What makes the token secure is that the payload is signed. If somebody tried to forge or tamper with the payload in a token, then the signature would be invalidated, and to generate a new signature the secret key is needed. When a token is verified, the contents of the payload are decoded and returned back to the caller. If the token's signature was validated, then the payload can be trusted as authentic.

The payload that I'm going to use for the password reset tokens is going to have the format {'reset_password': user_id, 'exp': token_expiration}. The exp field is standard for JWTs and if present it indicates an expiration time for the token. If a token has a valid signature, but it is past its expiration timestamp, then it will also be considered invalid. For the password reset feature, I'm going to give these tokens 10 minutes of life.

When the user clicks on the emailed link, the token is going to be sent back to the application as part of the URL, and the first thing the view function that handles this URL will do is to verify it. If the signature is valid, then the user can be identified by the ID stored in the payload. Once the user's identity is known, the application can ask for a new password and set it on the user's account.

Since these tokens belong to users, I'm going to write the token generation and verification functions as methods in the User model:

app/models.py: Reset password token methods.

from time import time
import jwt
from app import app

class User(UserMixin, db.Model):
    # ...

    def get_reset_password_token(self, expires_in=600):
        return jwt.encode(
            {'reset_password': self.id, 'exp': time() + expires_in},
            app.config['SECRET_KEY'], algorithm='HS256').decode('utf-8')

    def verify_reset_password_token(token):
            id = jwt.decode(token, app.config['SECRET_KEY'],
        return User.query.get(id)

The get_reset_password_token() function generates a JWT token as a string. Note that the decode('utf-8') is necessary because the jwt.encode() function returns the token as a byte sequence, but in the application it is more convenient to have the token as a string.

The verify_reset_password_token() is a static method, which means that it can be invoked directly from the class. A static method is similar to a class method, with the only difference that static methods do not receive the class as a first argument. This method takes a token and attempts to decode it by invoking PyJWT's jwt.decode() function. If the token cannot be validated or is expired, an exception will be raised, and in that case I catch it to prevent the error, and then return None to the caller. If the token is valid, then the value of the reset_password key from the token's payload is the ID of the user, so I can load the user and return it.

Sending a Password Reset Email

Now that I have the tokens, I can generate the password reset emails. The send_password_reset_email() function relies on the send_email() function I wrote above.

app/email.py: Send password reset email function.

from flask import render_template
from app import app

# ...

def send_password_reset_email(user):
    token = user.get_reset_password_token()
    send_email('[Microblog] Reset Your Password',
                                         user=user, token=token),
                                         user=user, token=token))

The interesting part in this function is that the text and HTML content for the emails is generated from templates using the familiar render_template() function. The templates receive the user and the token as arguments, so that a personalized email message can be generated. Here is the text template for the reset password email:

app/templates/email/reset_password.txt: Text for password reset email.

Dear {{ user.username }},

To reset your password click on the following link:

{{ url_for('reset_password', token=token, _external=True) }}

If you have not requested a password reset simply ignore this message.


The Microblog Team

And here is the nicer HTML version of the same email:

app/templates/email/reset_password.html: HTML for password reset email.

<p>Dear {{ user.username }},</p>
    To reset your password
    <a href="{{ url_for('reset_password', token=token, _external=True) }}">
        click here
<p>Alternatively, you can paste the following link in your browser's address bar:</p>
<p>{{ url_for('reset_password', token=token, _external=True) }}</p>
<p>If you have not requested a password reset simply ignore this message.</p>
<p>The Microblog Team</p>

The reset_password route that is referenced in the url_for() call in these two email templates does not exist yet, this will be added in the next section. The _external=True argument that I included in the url_for() calls in both templates is also new. The URLs that are generated by url_for() by default are relative URLs, so for example, the url_for('user', username='susan') call would return /user/susan. This is normally sufficient for links that are generated in web pages, because the web browser takes the remaining parts of the URL from the current page. When sending a URL by email however, that context does not exist, so fully qualified URLs need to be used. When _external=True is passed as an argument, complete URLs are generated, so the previous example would return http://localhost:5000/user/susan, or the appropriate URL when the application is deployed on a domain name.

Resetting a User Password

When the user clicks on the email link, a second route associated with this feature is triggered. Here is the password request view function:

app/routes.py: Password reset view function.

from app.forms import ResetPasswordForm

@app.route('/reset_password/<token>', methods=['GET', 'POST'])
def reset_password(token):
    if current_user.is_authenticated:
        return redirect(url_for('index'))
    user = User.verify_reset_password_token(token)
    if not user:
        return redirect(url_for('index'))
    form = ResetPasswordForm()
    if form.validate_on_submit():
        flash('Your password has been reset.')
        return redirect(url_for('login'))
    return render_template('reset_password.html', form=form)

In this view function I first make sure the user is not logged in, and then I determine who the user is by invoking the token verification method in the User class. This method returns the user if the token is valid, or None if not. If the token is invalid I redirect to the home page.

If the token is valid, then I present the user with a second form, in which the new password is requested. This form is processed in a way similar to previous forms, and as a result of a valid form submission, I invoke the set_password() method of User to change the password, and then redirect to the login page, where the user can now login.

Here is the ResetPasswordForm class:

app/forms.py: Password reset form.

class ResetPasswordForm(FlaskForm):
    password = PasswordField('Password', validators=[DataRequired()])
    password2 = PasswordField(
        'Repeat Password', validators=[DataRequired(), EqualTo('password')])
    submit = SubmitField('Request Password Reset')

And here is the corresponding HTML template:

app/templates/reset_password.html: Password reset form template.

{% extends "base.html" %}

{% block content %}
    <h1>Reset Your Password</h1>
    <form action="" method="post">
        {{ form.hidden_tag() }}
            {{ form.password.label }}<br>
            {{ form.password(size=32) }}<br>
            {% for error in form.password.errors %}
            <span style="color: red;">[{{ error }}]</span>
            {% endfor %}
            {{ form.password2.label }}<br>
            {{ form.password2(size=32) }}<br>
            {% for error in form.password2.errors %}
            <span style="color: red;">[{{ error }}]</span>
            {% endfor %}
        <p>{{ form.submit() }}</p>
{% endblock %}

The password reset feature is now complete, so make sure you try it.

Asynchronous Emails

If you are using the simulated email server that Python provides you may not have noticed this, but sending an email slows the application down considerably. All the interactions that need to happen when sending an email make the task slow, it usually takes a few seconds to get an email out, and maybe more if the email server of the addressee is slow, or if there are multiple addressees.

What I really want is for the send_email() function to be asynchronous. What does that mean? It means that when this function is called, the task of sending the email is scheduled to happen in the background, freeing the send_email() to return immediately so that the application can continue running concurrently with the email being sent.

Python has support for running asynchronous tasks, actually in more than one way. The threading and multiprocessing modules can both do this. Starting a background thread for email being sent is much less resource intensive than starting a brand new process, so I'm going to go with that approach:

app/email.py: Send emails asynchronously.

from threading import Thread
# ...

def send_async_email(app, msg):
    with app.app_context():

def send_email(subject, sender, recipients, text_body, html_body):
    msg = Message(subject, sender=sender, recipients=recipients)
    msg.body = text_body
    msg.html = html_body
    Thread(target=send_async_email, args=(app, msg)).start()

The send_async_email function now runs in a background thread, invoked via the Thread() class in the last line of send_email(). With this change, the sending of the email will run in the thread, and when the process completes the thread will end and clean itself up. If you have configured a real email server, you will definitely notice a speed improvement when you press the submit button on the password reset request form.

You probably expected that only the msg argument would be sent to the thread, but as you can see in the code, I'm also sending the application instance. When working with threads there is an important design aspect of Flask that needs to be kept in mind. Flask uses contexts to avoid having to pass arguments across functions. I'm not going to go into a lot of detail on this, but know that there are two types of contexts, the application context and the request context. In most cases, these contexts are automatically managed by the framework, but when the application starts custom threads, contexts for those threads may need to be manually created.

There are many extensions that require an application context to be in place to work, because that allows them to find the Flask application instance without it being passed as an argument. The reason many extensions need to know the application instance is because they have their configuration stored in the app.config object. This is exactly the situation with Flask-Mail. The mail.send() method needs to access the configuration values for the email server, and that can only be done by knowing what the application is. The application context that is created with the with app.app_context() call makes the application instance accessible via the current_app variable from Flask.


  • #51 Ernie Peters said 2018-07-27T16:25:26Z

    I am up to the asynchronous email section but before I go further, I can't get flask to send a reset password email to my gmail. I have compared my code to yours and the only difference is that mine code classes where in a slightly different order. When I hit the send password reset button. No errors are thrown and all seems like it is going well except for I am not receiving an email. I went back to chapter 7 and followed the example using the flask shell and I managed to send an email but I don't know how to troubleshoot it now that I have it in my code. Gmail security settings are set to allow less trusted apps (for now).

  • #52 Boudhayan Dev said 2018-07-29T06:06:48Z

    Hi, I had a doubt regarding the tokens that you generated. So, I understood the entire workflow and how the validation of the tokens take place based on a timeout that we define. But what I fail to understand is that where is the token being saved so that it can be used again for validation i.e when the user checks his e-mail and clicks on the follow up link ? Right now it seems that the generated token is saved in "run-time memory" (?? Im not sure this is the correct term ). So, what happens when we have 1000 users sending out password reset request at the same time. Wouldn't it create 1000 tokens and increase the memory usage ? Also, is it possible to store the tokens in the User database and when the time comes to retrieve it for verification, we can just use database queries for that ?

  • #53 Holger said 2018-07-29T21:22:16Z

    Hi Miguel, I have a question regarding the way the token is processed. Is there a specific reason why you made it part of the route via `reset_password/<token>`, instead of as a request parameter? Since it's only a "nuisance" and not any kind of resource, I tend to think that making the token a request parameter would be more natural. From a design/security point of view, is there any relevant difference between the two approaches? Thanks for the great tutorial!

  • #54 Miguel Grinberg said 2018-07-30T20:35:58Z

    @Ernie: Can you send emails to the SMTP development server?

  • #55 Miguel Grinberg said 2018-07-30T20:51:04Z

    @Boudhayan: The tokens that I'm using are JWTs (JSON Web Tokens). They do not need to be saved anywhere, as they are self-contained. The data that is associated with the token is stored in the token itself.

  • #56 Miguel Grinberg said 2018-07-30T20:52:37Z

    @Holger: making it a URL part forces the token to be required. You can also pass it as a query string argument, but then your view function will have to validate that the client sent the token.

  • #57 Richard Henderson said 2018-08-01T05:32:39Z

    Hey Miguel, great tutorial so far! I didn't think it would take me this long, probably because I'm just a noob and sometimes have spelling errors, but I make sure to double check most of the time! Anyways, here's my problem. - - [31/Jul/2018 22:16:31] "GET /reset_password_request HTTP/1.1" 200 - [2018-07-31 22:16:36,275] ERROR in app: Exception on /reset_password_request [POST] Traceback (most recent call last): File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask/app.py", line 2292, in wsgi_app response = self.full_dispatch_request() File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask/app.py", line 1815, in full_dispatch_request rv = self.handle_user_exception(e) File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask/app.py", line 1718, in handle_user_exception reraise(exc_type, exc_value, tb) File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask/_compat.py", line 35, in reraise raise value File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask/app.py", line 1813, in full_dispatch_request rv = self.dispatch_request() File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask/app.py", line 1799, in dispatch_request return self.view_functions[rule.endpoint](**req.view_args) File "/home/motu/Projects/nuevoproject/app/routes.py", line 158, in reset_password_request send_password_reset_email(user) File "/home/motu/Projects/nuevoproject/app/email.py", line 20, in send_password_reset_email user=user, token=token)) File "/home/motu/Projects/nuevoproject/app/email.py", line 10, in send_email mail.send(msg) File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask_mail.py", line 491, in send with self.connect() as connection: File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask_mail.py", line 144, in __enter__ self.host = self.configure_host() File "/home/motu/Projects/nuevoproject/venv/lib/python3.6/site-packages/flask_mail.py", line 163, in configure_host host.starttls() File "/usr/lib/python3.6/smtplib.py", line 752, in starttls "STARTTLS extension not supported by server.") smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server. I'm pretty stuck here. I originally had another problem with setting up the email server with google. I gave up on that and did the "dummy" web server trick with a second terminal. I thought this would fix things but I ended up running into this issue. I havne't really had much luck trying to figure this out with stackoverflow. I'm guessing it has something to do with our config.py file. The line where it states 'MAIL_USE_TLS = os.environ.get('MAIL_USE_TLS') is not None'. Problem is that my config file is the exact same as yours so I don't really know what to do haha. Help would be appreciated!

  • #58 Miguel Grinberg said 2018-08-01T22:39:17Z

    @Richard: You have the MAIL_USE_TLS environment variable set. This variable needs to be deleted from the environment, because the development SMTP server does not support TLS.

  • #59 nick said 2018-08-04T09:03:27Z

    Hello, Miguel, when I submit email for password reset I get the following error kindly help me here File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 2309, in __call__ return self.wsgi_app(environ, start_response) File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 2295, in wsgi_app response = self.handle_exception(e) File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 1741, in handle_exception reraise(exc_type, exc_value, tb) File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/_compat.py", line 35, in reraise raise value File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 2292, in wsgi_app response = self.full_dispatch_request() File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 1815, in full_dispatch_request rv = self.handle_user_exception(e) File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 1718, in handle_user_exception reraise(exc_type, exc_value, tb) File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/_compat.py", line 35, in reraise raise value File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 1813, in full_dispatch_request rv = self.dispatch_request() File "/home/kino/Desktop/microblog/microblogproject/lib/python3.6/site-packages/flask/app.py", line 1799, in dispatch_request return self.view_functions[rule.endpoint](**req.view_args) File "/home/kino/Desktop/microblog/app/routes.py", line 163, in reset_password_request send_password_reset_email(user) File "/home/kino/Desktop/microblog/app/email.py", line 18, in send_password_reset_email token = user.get_reset_password_token() TypeError: get_reset_password_token() missing 1 required positional argument: 'token'

  • #60 Miguel Grinberg said 2018-08-04T21:35:50Z

    @nick: the only argument to get_reset_password_token is expires_in, and it should have a default value. Make sure this is correct in your code, sounds like you have an argument that does not have a default value.

  • #61 Varoon said 2018-08-15T00:49:03Z

    File "C:\Users\user\AppData\Local\Programs\Python\Python37\lib\smtplib.py", line 359, in send raise SMTPServerDisconnected('please run connect() first') smtplib.SMTPServerDisconnected: please run connect() first part of my output.. Please help

  • #62 Miguel Grinberg said 2018-08-15T07:02:45Z

    @Varoon: not sure. Maybe an issue with the SMTP server that you are using? Try the development SMTP server to make sure your code is okay.

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