The Flask Mega-Tutorial, Part X: Email Support

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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.

You are reading the 2024 edition of the Flask Mega-Tutorial. The complete course is also available to order in e-book and paperback formats from Amazon. Thank you for your support!

If you are looking for the 2018 edition of this course, you can find it here.

For your reference, here is the complete list of articles in this series:

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 will then need 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. 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 options I mentioned in Chapter 7. If you want to use an emulated email server, then you can start the same SMTP debugging server used earlier in a second terminal with the following command:

(venv) $ aiosmtpd -n -c aiosmtpd.handlers.Debugging -l localhost:8025

To configure the application to use 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.

Unfortunately the security features in your Gmail account may prevent the application from sending emails through it. Some accounts allow it when you explicitly allow "less secure apps" access to your Gmail account, but this isn't always available. You can read about this here.

If you'd like to use a real email server, but don't want to complicate yourself with the Gmail configuration, SendGrid is a good option that gives you 100 emails per day using a free account.

Flask-Mail Usage

To learn how Flask-Mail works, I'll show you how to send an email from a Python shell session. 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 email 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.

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
    mail.send(msg)

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.

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

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() }}
        <p>
            {{ form.email.label }}<br>
            {{ form.email(size=64) }}<br>
            {% for error in form.email.errors %}
            <span style="color: red;">[{{ error }}]</span>
            {% endfor %}
        </p>
        <p>{{ form.submit() }}</p>
    </form>
{% 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 = db.session.scalar(
            sa.select(User).where(User.email == form.email.data))
        if user:
            send_password_reset_email(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. The send_password_reset_email() helper function performs this task. I will show you this function next.

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
'eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.eyJhIjoiYiJ9.dvOo58OBDHiuSHD4uW88nfJik_sfUHq1mDi4G0'
>>> 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 Flask configuration. The algorithm argument specifies how the token signature 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 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')

    @staticmethod
    def verify_reset_password_token(token):
        try:
            id = jwt.decode(token, app.config['SECRET_KEY'],
                            algorithms=['HS256'])['reset_password']
        except:
            return
        return db.session.get(User, id)

The get_reset_password_token() function returns a JWT token as a string, which is generated directly by the jwt.encode() function.

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 is 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

The send_password_reset_email() function relies on the send_email() function I wrote above to generate the password reset emails.

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',
               sender=app.config['ADMINS'][0],
               recipients=[user.email],
               text_body=render_template('email/reset_password.txt',
                                         user=user, token=token),
               html_body=render_template('email/reset_password.html',
                                         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.

To distinguish email templates from regular HTML templates, let's create a email subdirectory inside templates:

(venv) $ mkdir app/templates/email

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.

Sincerely,

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.

<!doctype html>
<html>
    <body>
        <p>Dear {{ user.username }},</p>
        <p>
            To reset your password
            <a href="{{ url_for('reset_password', token=token, _external=True) }}">
                click here
            </a>.
        </p>
        <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>Sincerely,</p>
        <p>The Microblog Team</p>
    </body>
</html>

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 that only include the path portion of the URL. This is normally sufficient for links that are generated in web pages, because the web browser completes the URL by taking the missing parts from the URL in the address bar. 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():
        user.set_password(form.password.data)
        db.session.commit()
        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 log in.

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() }}
        <p>
            {{ form.password.label }}<br>
            {{ form.password(size=32) }}<br>
            {% for error in form.password.errors %}
            <span style="color: red;">[{{ error }}]</span>
            {% endfor %}
        </p>
        <p>
            {{ form.password2.label }}<br>
            {{ form.password2(size=32) }}<br>
            {% for error in form.password2.errors %}
            <span style="color: red;">[{{ error }}]</span>
            {% endfor %}
        </p>
        <p>{{ form.submit() }}</p>
    </form>
{% endblock %}

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

Asynchronous Emails

If you are using the debugging email server you may not have noticed this, but sending an email for real slows the application down considerably. All the interactions that need to happen when sending an email make the task slow, usually taking 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 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():
        mail.send(msg)


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 yet, 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 Flask, 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.

Continue on to the next chapter.

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15 comments
  • #1 ArrayOfLilly said

    I think Google permits to send emails beside normal security settings, if you turned on the 2FA and generate a unique app password for this purpose. Unless you mean exactly that risk, but what was a long time ago that literally had to be set up this is gone.

    I found: "As of 2022 May 22 Google removed the ability to allow less secure devices."
    The app password feature is now found in the same "Signing in to Google" area, under the 2FA setting.

  • #2 Neelarghya Kundu said

    Why do I get "The syntax of command is incorrect", when using set MAIL_USERNAME=<your-gmail-username> command ?

  • #3 Miguel Grinberg said

    @Neelarghya: My guess is that the shell that you are using needs a different syntax to set an environment variable.

  • #4 Punch said

    I'm trying to figure out how to boot off all active sessions when the user resets its password. I guess you could alter the user loader you provide to Flask-Login to use a changeable secondary ID, to invalidate the local remember me token upon password reset, but what if one of the sessions doesn't enable remember me? Flask-Login calls the user loader only to validate the remember me cookie, doesn't it?
    Any pointers are appreciated. Great blog by the way!

  • #5 Miguel Grinberg said

    @Punch: what I would do: 1. Store an additional field in the user table with the timestamp of the last password change. 2. Store the timestamp of the log in in the user session. 3. In the user loader function, make sure that login timestamp >= password change timestamp before returning the user.

  • #6 Punch said

    Thanks! I guess I misunderstood the flask-login user loader decorator/callback, it does make calls to validate the user on the session cookie, too. Using a timestamp is working like a charm.

    I was thinking about supporting multiple sessions in that scenario (sessions are only invalidated after pass reset) but I guess instead of the log in timestamp, l'd have to use an obfuscated/hashed pass-last-modified timestamp on the session cookie, so I could keep more than one session alive. Timestamp disclosure is bad in this scenario, and I'd probably have to use another secret key to hash that info (can't reuse werkzeug's generate_password_hash then).

    Or maybe it would be time to use a real IdP through OAuth in that case. Hehe.

  • #7 Miguel Grinberg said

    @Punch: What I proposed should allow multiple sessions to be active, as long as they were all created after the password change. Maybe I'm not fully understanding what you want to do, but I don't see why multiple sessions cannot coexist.

  • #8 Punch said

    Actually I forgot I had timestamps be updated after every log in action, too. Classic mental lapse. It's working great with multiple sessions now :)

  • #9 Eldar said

    At the end, I was able to send email ony watching your video (#Flask 2 about contexts) and writing the code in application context;

    from flask_mail import Message
    from app import mail
    with app.app_context():
    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)

  • #10 varad said

    Hey I have to export all this environment variables every time I restart my vs code, is this is a bug or it's just have to do this way?

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

  • #11 Miguel Grinberg said

    @varad: your shell provides options run code when a new shell is opened, including setting environment variables, so you can do this according to your shell, for example by setting your variables in a .bashrc or .zshrc file. Later in this tutorial you will also learn how to work with a .env file to store environment variables associated with your project.

  • #12 Grant said

    Little odd, but when I tried to create the identical JWT token on a Python shell using identical commands, I got 'eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.eyJhIjoiYiJ9.dvOo58OBDHiuSHD4uW88nfJikhYAXc_sfUHq1mDi4G0' while this document produces 'eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.eyJhIjoiYiJ9.dvOo58OBDHiuSHD4uW88nfJik_sfUHq1mDi4G0'. Also, when I go to the linked JWT debugger, I get the former, and not the latter. IOW I cannot produce the same token you did as an example.

  • #13 Miguel Grinberg said

    @Grant: The example JWT I show here is just that, an example. It is only useful so that you have an idea of what the JWT looks like, I do not claim that it is accurate and that you should get the exact same one. If you get a different one it does not matter, as long as it can be decoded!

  • #14 TheBlack said

    Hello, in app.models.User.verify_reset_password_token() function
    (https://github.com/miguelgrinberg/microblog/blob/a3cc2beff1ec8d49b99dab7fa0f4dd03b1614e4c/app/models.py#L105)
    is it required to use "except:" (broad exception clause) instead of "except jwt.PyJWTError:"? Or we expect there any other exceptions than jwt module may raise?
    Thanks in advance.

  • #15 Miguel Grinberg said

    @TheBlack: It isn't required to use a broad exception clause, it is just a choice. If you prefer to use a scoped exception clause that is fine, but you have to be prepared for your application to crash if there is any condition that you may not be aware of inside the PyJWT library (including bugs, present or in the future) that may raise a different exception. My preference is that in this case I want to be 100% sure that if PyJWT cannot process the token I handle the error and prevent unexpected crashes, but I recognize this is a personal preference.

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