EmailMessage().add_attachment() doesn't work for htm... | python/cpython

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Bug report

I am trying to send a 1.5 MB .html file using from email.message import EmailMessage through the add_attachment method. If the filename ends in ".html", the email will not be sent, nor any warning/exception is raised.

This is the code that I am using:

message["From"] = sender_email
message["To"] = ", ".join(receiver_email)
message.set_content(text)

context = ssl.create_default_context()

for i, fn in enumerate([filename, mapname]):
    print("Processing filename", fn)
    with open(fn, "rb") as attachment:
        content = attachment.read()
        ctype, encoding = mimetypes.guess_type(fn)
        maintype, subtype = ctype.split("/", 1)
        message.add_attachment(
            content,
            maintype=maintype,
            subtype=subtype,
            filename=f"{i}_{fn}",
        )

with smtplib.SMTP_SSL("smtp.gmail.com", port, context=context) as server:
    server.login(sender_email, password)
    server.send_message(message)
    print("Sent!")

You see that I have two filenames, one is filename and the other one is mapname. filename is a csv file and mapname is an html file. If I only use the filename, the mail is sent. If I add mapname, the mail is not sent. If I only use mapname, the email is not sent either.

If the filename is changed: f"{i}_{fn.split('.')[0]}", so that the extension is removed, the email is sent! This shows that the HTML is not corrupt, it's just because of the extension! Also, I tried sending a simple html such as this one:

msg_content = """
<html><body>
  Hello world
</body></html>"""
content = bytes(msg_content, "utf-8")
ctype, encoding = mimetypes.guess_type("second.html")
maintype, subtype = ctype.split("/", 1)
message.add_attachment(
    content,
    maintype=maintype,
    subtype=subtype,
    filename="second.html",
)

And it still does not work.

Your environment

I'm using a virtual environment with Python version Python 3.9.10. The architecture is arm64. pip freeze shows:

absl-py==1.0.0
alembic==1.7.6
anyio==3.5.0
appnope==0.1.2
argon2-cffi==21.3.0
argon2-cffi-bindings==21.2.0
asttokens==2.0.5
attrs==21.4.0
autopage==0.5.0
Babel==2.9.1
backcall==0.2.0
beautifulsoup4==4.10.0
beniget==0.4.1
black==22.1.0
bleach==4.1.0
bokeh==2.4.2
certifi==2021.10.8
cffi==1.15.0
charset-normalizer==2.0.12
chex==0.1.1
click==8.0.4
cliff==3.10.1
cmaes==0.8.2
cmd2==2.4.0
colorlog==6.6.0
cycler==0.11.0
Cython==0.29.28
debugpy==1.5.1
decorator==5.1.1
defusedxml==0.7.1
dm-tree==0.1.6
dnspython==2.2.1
entrypoints==0.4
executing==0.8.3
flatbuffers==2.0
flax==0.4.0
fonttools==4.30.0
gast==0.5.3
idna==3.3
ipykernel==6.9.1
ipython==8.1.1
ipython-genutils==0.2.0
jedi==0.18.1
Jinja2==3.1.1
joblib==1.1.0
json5==0.9.6
jsonschema==4.4.0
jupyter-client==7.1.2
jupyter-core==4.9.2
jupyter-server==1.16.0
jupyterlab==3.3.2
jupyterlab-pygments==0.1.2
jupyterlab-server==2.12.0
kiwisolver==1.3.2
lightgbm==3.3.2
Mako==1.2.0
MarkupSafe==2.1.0
matplotlib==3.5.1
matplotlib-inline==0.1.3
miceforest==5.3.0
mistune==0.8.4
msgpack==1.0.3
mypy-extensions==0.4.3
nbclassic==0.3.7
nbclient==0.5.13
nbconvert==6.4.5
nbformat==5.2.0
nest-asyncio==1.5.4
notebook==6.4.10
notebook-shim==0.1.0
numpy==1.22.3
opt-einsum==3.3.0
optax==0.1.1
optuna==2.10.0
packaging==21.3
pandas==1.3.5
pandocfilters==1.5.0
parso==0.8.3
pathspec==0.9.0
pbr==5.8.1
pexpect==4.8.0
pickleshare==0.7.5
Pillow==9.0.1
platformdirs==2.5.1
ply==3.11
prettytable==3.2.0
prometheus-client==0.13.1
prompt-toolkit==3.0.28
ptyprocess==0.7.0
pure-eval==0.2.2
pybind11==2.9.1
pycparser==2.21
Pygments==2.11.2
pymongo==4.0.1
pyparsing==3.0.7
pyperclip==1.8.2
pyrsistent==0.18.1
python-dateutil==2.8.2
pythran==0.11.0
pytz==2021.3
PyYAML==6.0
pyzmq==22.3.0
requests==2.27.1
scipy==1.9.0.dev0+1659.2656ccb
Send2Trash==1.8.0
six==1.16.0
sniffio==1.2.0
soupsieve==2.3.1
SQLAlchemy==1.4.32
stack-data==0.2.0
stevedore==3.5.0
terminado==0.13.3
testpath==0.6.0
threadpoolctl==3.1.0
tomli==2.0.1
toolz==0.11.2
tornado==6.1
tqdm==4.63.0
traitlets==5.1.1
typing_extensions==4.1.1
urllib3==1.26.9
wcwidth==0.2.5
webencodings==0.5.1
websocket-client==1.3.2

Inizia dal punto di ingresso email.message.EmailMessage.add_attachment e riproduci il problema usando l’esempio HTML minimo, verificando la gestione del nome del file e del tipo MIME. Conferma il comportamento previsto per gli allegati HTML, quindi aggiungi una copertura di regressione che dimostri che un allegato .html viene inviato correttamente.

Scritto dal modello di indicizzazione a partire dal testo della issue.

EmailMessage().add_attachment() doesn't work for html files

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