diff --git a/common/djangoapps/util/log_sensitive.py b/common/djangoapps/util/log_sensitive.py
new file mode 100644
index 0000000000..8874b7f518
--- /dev/null
+++ b/common/djangoapps/util/log_sensitive.py
@@ -0,0 +1,199 @@
+"""
+Utilities for logging sensitive debug information such as authentication tokens.
+
+Usage:
+
+1. Generate keys using ``python3 -m common.djangoapps.util.log_sensitive gen-keys``
+2. Follow the instructions it prints out, and pay close attention to the warning
+   at the end of the output
+3. When logging sensitive information, use like so::
+
+     logger.info(
+         "Received invalid auth token %s in Authorization header",
+         encrypt_for_log(token, settings.<YOUR_DEBUG_PUBLIC_KEY>)
+     )
+
+   This will log a message like::
+
+     Received invalid auth token [encrypted: ZXI...fFo=|IYS...1KA==] in Authorization header
+
+4. If you need to decrypt one of these messages, save the encrypted portion
+   to file, retrieve the securely held private key, and run
+   ``python3 -m common.djangoapps.util.log_sensitive decrypt --help``
+   for instructions.
+"""
+
+from base64 import b64decode, b64encode
+
+import click
+from nacl.public import Box, PrivateKey, PublicKey
+
+# Background:
+#
+# The NaCl "Box" construction provides asymmetric encryption, allowing
+# the sender to encrypt something for a recipient without having a
+# shared secret. This encryption is authenticated, meaning that the
+# recipient verifies that the message matches the sender's public key
+# (proof of sender). But it's also *repudiable* authentication; the
+# design allows both the sender and the receiver to read (or have
+# created!) the encrypted message, so the receipient can't prove to
+# anyone *else* that the sender was the author.
+#
+# Why we use ephemeral sender keys:
+#
+# The Box is normally an ideal construction to use for
+# communications. However, we don't want the logger to be able to read
+# the messages it writes, especially not messages from a different
+# server instance or from days or weeks ago. Only developers (or
+# others) in possession of the recipient keypair should be able to
+# read it, not anyone who compromises a server at some later
+# date. Luckily, we also don't care about authenticating the logged
+# messages as truly being from the server! The solution is for each
+# server to create a fresh public/private keypair at startup and to
+# include a copy of the public key in any encrypted logs it writes.
+
+
+# Generate an ephemeral private key for the logger to use during this
+# logging session.
+logger_private_key = PrivateKey.generate()
+
+
+def encrypt_for_log(message, reader_public_key_b64):
+    """
+    Encrypt a message so that it can be logged using the given public key,
+    but only read by someone possessing the matching private key. The
+    public key is provided in base64.
+
+    A separate keypair should be used for each recipient or purpose.
+
+    Returns a string <sender public key> "|" <ciphertext> wrapped in
+    some framing text "[encrypted: ...]"; the inner string can be
+    decrypted with decrypt_log_message.
+    """
+    reader_public_key = PublicKey(b64decode(reader_public_key_b64))
+
+    encrypted = Box(logger_private_key, reader_public_key).encrypt(message.encode())
+
+    pubkey = logger_private_key.public_key
+    combined = b64encode(bytes(pubkey)).decode() + '|' + b64encode(encrypted).decode()
+    # The goal of this framing text is to make it always clear in log
+    # messages that the information is encrypted
+    return f"[encrypted: {combined}]"
+
+
+def decrypt_log_message(encrypted_message, reader_private_key_b64):
+    """
+    Decrypt a message using the private key that has been stored somewhere
+    secure and *not* on the server.
+    """
+    reader_private_key = PrivateKey(b64decode(reader_private_key_b64))
+    sender_public_key_data, encrypted_raw = \
+        [b64decode(part) for part in encrypted_message.split('|', 1)]
+    return Box(reader_private_key, PublicKey(sender_public_key_data)).decrypt(encrypted_raw).decode()
+
+
+def generate_reader_keys():
+    """
+    Utility method for generating a public/private keypair for use with these
+    logging functions.
+    """
+    reader_private_key = PrivateKey.generate()
+    return {
+        'public': b64encode(bytes(reader_private_key.public_key)).decode(),
+        'private': b64encode(bytes(reader_private_key)).decode(),
+    }
+
+
+@click.group()
+def cli():
+    pass
+
+
+@click.command('gen-keys', help="Generate keypair")
+def cli_gen_keys():
+    """
+    Generate and print a keypair for handling sensitive log messages.
+    """
+    reader_keys = generate_reader_keys()
+    public_64 = reader_keys['public']
+    private_64 = reader_keys['private']
+    print(
+        "This is your PUBLIC key, which should be included in the server's "
+        "configuration. Create a separate setting (and keypair) for each "
+        "distinct project or team. This value does not need special protection:"
+        "\n\n"
+        f"  settings.<YOUR_DEBUG_PUBLIC_KEY> = \"{public_64}\""
+        "\n\n"
+        "This is your PRIVATE key, which must never be present on the server "
+        "and should instead be kept encrypted in a separate, safe place "
+        "such as a password manager:"
+        "\n\n"
+        f"  \"{private_64}\" (private)"
+        "\n\n"
+        "WARNING: Before logging anything sensitive, get a legal/compliance review to "
+        "ensure this is acceptable in your organization. Encryption is not "
+        "generally a replacement for retention policies or other privacy "
+        "safeguards; using this utility does not automatically make sensitive "
+        "information safe to handle."
+    )
+
+
+@click.command('decrypt', help="""Decrypt a logged message.
+
+If possible, use bash process indirection to keep the private key from
+touching disk or shell history unencrypted. The safest way is to keep
+the private key in an encrypted file:
+
+    --private-key-file <(gpg2 --decrypt auth-logging-key.enc)
+
+Alternatively, you could copy it from a password manager to your
+clipboard and use a CLI clipboard tool to retrieve it:
+
+\b
+    --private-key-file <(xsel -bo) # Linux
+    --private-key-file <(pbpaste) # Mac
+
+Another option is to somehow get the private key into an environment
+variable and echo it out:
+
+    --private-key-file <(echo "$PRIVATE_KEY")
+
+The same techniques can also be used for the encrypted message data,
+which is less sensitive but should also be handled with care.
+""")
+@click.option(
+    '--private-key-file', type=click.File('r'), required=True,
+    help="Path to file containing reader's private key in Base64",
+)
+@click.option(
+    '--message-file', type=click.File('r'), required=True,
+    help="Path to file containing encrypted message, or - for stdin",
+)
+def cli_decrypt(private_key_file, message_file):
+    """
+    Decrypt a message and print it to stdout.
+    """
+    print(decrypt_log_message(message_file.read(), private_key_file.read()))
+
+
+@click.command('encrypt', help="Encrypt a one-off message (for testing)")
+@click.option('--public-key', help="Reader's public key, in Base64")
+@click.option(
+    '--message-file', type=click.File('r'), required=True,
+    help="Path to file containing message to encrypt, or - for stdin",
+)
+def cli_encrypt(public_key, message_file):
+    """
+    Encrypt a message to the provided public key and print it to stdout.
+
+    This is just intended for use when testing or experimenting with the decrypt command.
+    """
+    print(encrypt_for_log(message_file.read(), public_key))
+
+
+cli.add_command(cli_gen_keys)
+cli.add_command(cli_decrypt)
+cli.add_command(cli_encrypt)
+
+if __name__ == '__main__':
+    cli()
diff --git a/common/djangoapps/util/tests/test_log_sensitive.py b/common/djangoapps/util/tests/test_log_sensitive.py
new file mode 100644
index 0000000000..a13305c09a
--- /dev/null
+++ b/common/djangoapps/util/tests/test_log_sensitive.py
@@ -0,0 +1,28 @@
+"""
+Tests for util.logging
+"""
+
+import re
+from common.djangoapps.util.log_sensitive import decrypt_log_message, encrypt_for_log, generate_reader_keys
+
+
+def test_encryption_round_trip():
+    reader_keys = generate_reader_keys()
+    reader_public_64 = reader_keys['public']
+    reader_private_64 = reader_keys['private']
+
+    to_log = encrypt_for_log("Testing testing 1234", reader_public_64)
+    re_base64 = r'[a-zA-Z0-9/+=]'
+    assert re.fullmatch(f'\\[encrypted: {re_base64}+\\|{re_base64}+\\]', to_log)
+
+    to_decrypt = to_log.partition('[encrypted: ')[2].rstrip(']')
+
+    decrypted = decrypt_log_message(to_decrypt, reader_private_64)
+    assert decrypted == "Testing testing 1234"
+
+    # Also check that decryption still works if someone accidentally
+    # copies in the trailing framing "]" character, just as a
+    # nice-to-have. (base64 module should handle this already, since
+    # it stops reading at the first invalid base64 character.)
+    decrypted_again = decrypt_log_message(to_decrypt + ']', reader_private_64)
+    assert decrypted_again == "Testing testing 1234"
diff --git a/requirements/edx/base.in b/requirements/edx/base.in
index 9cd76900d8..18eee89990 100644
--- a/requirements/edx/base.in
+++ b/requirements/edx/base.in
@@ -133,6 +133,7 @@ pyjwkest
 PyJWT>=1.6.3
 pylti1p3                            # Required by content_libraries core library to suport LTI 1.3 launches
 pymongo                             # MongoDB driver
+PyNaCl                              # User-friendly cryptography (wrapper and bindings for libsodium)
 pynliner                            # Inlines CSS styles into HTML for email notifications
 python-dateutil
 python-Levenshtein
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index 6a4a120b53..78feab62c7 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -109,10 +109,12 @@ certifi==2021.10.8
     #   py2neo
     #   requests
 cffi==1.15.0
-    # via cryptography
+    # via
+    #   cryptography
+    #   pynacl
 chardet==4.0.0
     # via pysrt
-charset-normalizer==2.0.9
+charset-normalizer==2.0.10
     # via
     #   -r requirements/edx/paver.txt
     #   aiohttp
@@ -166,7 +168,7 @@ deprecated==1.2.13
     # via
     #   jwcrypto
     #   redis
-django==3.2.10
+django==3.2.11
     # via
     #   -c requirements/edx/../common_constraints.txt
     #   -c requirements/edx/../constraints.txt
@@ -784,6 +786,8 @@ pymongo==3.10.1
     #   event-tracking
     #   mongodbproxy
     #   mongoengine
+pynacl==1.4.0
+    # via -r requirements/edx/base.in
 pynliner==0.8.0
     # via -r requirements/edx/base.in
 pyparsing==3.0.6
@@ -943,6 +947,7 @@ six==1.16.0
     #   paver
     #   py2neo
     #   pyjwkest
+    #   pynacl
     #   python-dateutil
     #   python-memcached
     #   python-swiftclient
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index 5ae5dd20c2..760e45e1ea 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -149,11 +149,12 @@ cffi==1.15.0
     # via
     #   -r requirements/edx/testing.txt
     #   cryptography
+    #   pynacl
 chardet==4.0.0
     # via
     #   -r requirements/edx/testing.txt
     #   pysrt
-charset-normalizer==2.0.9
+charset-normalizer==2.0.10
     # via
     #   -r requirements/edx/testing.txt
     #   aiohttp
@@ -244,7 +245,7 @@ distlib==0.3.4
     # via
     #   -r requirements/edx/testing.txt
     #   virtualenv
-django==3.2.10
+django==3.2.11
     # via
     #   -c requirements/edx/../common_constraints.txt
     #   -c requirements/edx/../constraints.txt
@@ -1086,6 +1087,8 @@ pymongo==3.10.1
     #   event-tracking
     #   mongodbproxy
     #   mongoengine
+pynacl==1.4.0
+    # via -r requirements/edx/testing.txt
 pynliner==0.8.0
     # via -r requirements/edx/testing.txt
 pyparsing==3.0.6
@@ -1318,6 +1321,7 @@ six==1.16.0
     #   paver
     #   py2neo
     #   pyjwkest
+    #   pynacl
     #   python-dateutil
     #   python-memcached
     #   python-swiftclient
diff --git a/requirements/edx/django.txt b/requirements/edx/django.txt
index b0be5a81cf..c93648df5e 100644
--- a/requirements/edx/django.txt
+++ b/requirements/edx/django.txt
@@ -1 +1 @@
-django==3.2.10
+django==3.2.11
diff --git a/requirements/edx/doc.txt b/requirements/edx/doc.txt
index b85d7f1c5b..a898118d04 100644
--- a/requirements/edx/doc.txt
+++ b/requirements/edx/doc.txt
@@ -10,7 +10,7 @@ babel==2.9.1
     # via sphinx
 certifi==2021.10.8
     # via requests
-charset-normalizer==2.0.9
+charset-normalizer==2.0.10
     # via requests
 click==7.1.2
     # via
diff --git a/requirements/edx/paver.txt b/requirements/edx/paver.txt
index d1c32bf4b6..05218feea4 100644
--- a/requirements/edx/paver.txt
+++ b/requirements/edx/paver.txt
@@ -6,7 +6,7 @@
 #
 certifi==2021.10.8
     # via requests
-charset-normalizer==2.0.9
+charset-normalizer==2.0.10
     # via requests
 edx-opaque-keys==2.2.2
     # via -r requirements/edx/paver.in
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index f45e949598..7ed9f9f334 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -144,11 +144,12 @@ cffi==1.15.0
     # via
     #   -r requirements/edx/base.txt
     #   cryptography
+    #   pynacl
 chardet==4.0.0
     # via
     #   -r requirements/edx/base.txt
     #   pysrt
-charset-normalizer==2.0.9
+charset-normalizer==2.0.10
     # via
     #   -r requirements/edx/base.txt
     #   aiohttp
@@ -1021,6 +1022,8 @@ pymongo==3.10.1
     #   event-tracking
     #   mongodbproxy
     #   mongoengine
+pynacl==1.4.0
+    # via -r requirements/edx/base.txt
 pynliner==0.8.0
     # via -r requirements/edx/base.txt
 pyparsing==3.0.6
@@ -1244,6 +1247,7 @@ six==1.16.0
     #   paver
     #   py2neo
     #   pyjwkest
+    #   pynacl
     #   python-dateutil
     #   python-memcached
     #   python-swiftclient
diff --git a/scripts/xblock/requirements.txt b/scripts/xblock/requirements.txt
index 5e204ed6a5..313f9c6a55 100644
--- a/scripts/xblock/requirements.txt
+++ b/scripts/xblock/requirements.txt
@@ -6,7 +6,7 @@
 #
 certifi==2021.10.8
     # via requests
-charset-normalizer==2.0.9
+charset-normalizer==2.0.10
     # via requests
 idna==3.3
     # via requests