The Tool Desk
Outbyte PC Repair FREEClear out junk files and repair common Windows errorsFree Scan →Outbyte Driver Updater FREEScan for outdated or missing drivers - takes under a minuteDriver Scan →Use Python’s standard email package to build the message and smtplib to deliver it. If the picture should appear inside the message, create an HTML alternative, give the image a Content-ID, and reference that ID with cid:. If recipients should download the file, add it as a conventional attachment instead. The complete examples below support both choices and use STARTTLS for a typical SMTP submission connection.
Choose how the recipient should receive the image
| Goal | MIME approach | What the recipient sees |
|---|---|---|
| Show the picture in the message | HTML body plus a related image part and matching Content-ID | The mail client can render the image at the position of the <img> element |
| Offer the original file for download | Attachment part with attachment disposition | A file in the message’s attachment area |
| Do both | HTML/CID image and a separate attachment | Inline preview plus downloadable copy |
Inline rendering depends on the recipient’s mail client and its security settings. Always include useful alternative text and a plain-text body. A cid: image is embedded in the message; it is not a remotely hosted image that the client must fetch from a website.
Prerequisites and safe configuration
- Python 3 with the standard-library
email,smtplib,ssl,mimetypesandpathlibmodules. - An image file readable by the process, such as
image.pngorphoto.jpg. - An SMTP submission host, port and authentication method allowed by your mail provider. Hostnames, quotas, OAuth requirements and app-password rules differ by provider; use that provider’s current documentation.
- Credentials supplied through environment variables or a secret manager, not hard-coded in source control.
The Python email package constructs the message, while smtplib handles the SMTP conversation. Keeping those responsibilities separate makes it easier to test message construction without sending mail.
Send an inline image with HTML and Content-ID
This runnable script creates a plain-text fallback, an HTML alternative and a related image part. The value inside cid: is the Content-ID without angle brackets; the MIME header receives the bracketed ID generated by make_msgid().
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from email.message import EmailMessage
from email.utils import make_msgid
from pathlib import Path
import mimetypes
import os
import smtplib
import ssl
sender = os.environ["EMAIL_SENDER"]
recipient = os.environ["EMAIL_RECIPIENT"]
image_path = Path(os.environ.get("IMAGE_PATH", "image.png"))
# Generate the ID before writing the HTML body.
image_cid = make_msgid()
msg = EmailMessage()
msg["Subject"] = "An image from Python"
msg["From"] = sender
msg["To"] = recipient
msg.set_content(
"This message contains an image. If your mail client does not display "
"HTML, the image is also attached."
)
msg.add_alternative(
f"""<html><body>
<p>Here is the image:</p>
<img src="cid:{image_cid[1:-1]}" alt="Image sent by Python">
</body></html>""",
subtype="html",
)
# The last payload is the HTML alternative.
html_part = msg.get_payload()[-1]
image_bytes = image_path.read_bytes()
mime_type, _ = mimetypes.guess_type(image_path.name)
if mime_type is None or not mime_type.startswith("image/"):
raise ValueError(f"Could not determine an image MIME type for {image_path}")
maintype, subtype = mime_type.split("/", 1)
html_part.add_related(
image_bytes,
maintype=maintype,
subtype=subtype,
cid=image_cid,
filename=image_path.name,
)
smtp_host = os.environ["SMTP_HOST"]
smtp_port = int(os.environ.get("SMTP_PORT", "587"))
password = os.environ["SMTP_PASSWORD"]
context = ssl.create_default_context()
with smtplib.SMTP(smtp_host, smtp_port, timeout=90) as smtp:
smtp.ehlo()
smtp.starttls(context=context)
smtp.ehlo() # Required after the TLS upgrade before authentication.
smtp.login(sender, password)
smtp.send_message(msg)
print("Message submitted")Install no third-party package for this example. Set the variables before running (the exact values come from your provider):
export EMAIL_SENDER='[email protected]'
export EMAIL_RECIPIENT='[email protected]'
export SMTP_HOST='smtp.example.com'
export SMTP_PORT='587'
export SMTP_PASSWORD='use-a-provider-approved-secret'
export IMAGE_PATH='image.png'
python send_image.pyWhy the Content-ID details matter
make_msgid() returns an ID in angle brackets, suitable for the MIME Content-ID header. HTML uses the same identifier without those brackets: cid:identifier. A mismatch produces a broken-image icon even though the message was accepted by SMTP.
add_related() creates or appends to a multipart/related section. With no attachment disposition, the image is treated as an inline resource. The HTML part and its related image must be kept together; adding the image to the top-level message can prevent clients from resolving the CID.
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Send the image as a downloadable attachment
For an attachment, you do not need HTML or a Content-ID. Build a normal text message and call add_attachment(). The method marks the part as an attachment by default.
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from email.message import EmailMessage
from pathlib import Path
import mimetypes
import os
import smtplib
import ssl
sender = os.environ["EMAIL_SENDER"]
recipient = os.environ["EMAIL_RECIPIENT"]
image_path = Path("image.jpg")
msg = EmailMessage()
msg["Subject"] = "Your requested photo"
msg["From"] = sender
msg["To"] = recipient
msg.set_content("The requested image is attached.")
mime_type, _ = mimetypes.guess_type(image_path.name)
if mime_type is None or not mime_type.startswith("image/"):
raise ValueError("The file does not have a recognized image MIME type")
maintype, subtype = mime_type.split("/", 1)
msg.add_attachment(
image_path.read_bytes(),
maintype=maintype,
subtype=subtype,
filename=image_path.name,
)
context = ssl.create_default_context()
with smtplib.SMTP(os.environ["SMTP_HOST"], int(os.environ.get("SMTP_PORT", "587")), timeout=90) as smtp:
smtp.ehlo()
smtp.starttls(context=context)
smtp.ehlo()
smtp.login(sender, os.environ["SMTP_PASSWORD"])
smtp.send_message(msg)Use the attachment route when the original bytes matter more than an in-message preview, when the recipient may use a text-only client, or when your HTML design is not needed. To provide both experiences, retain the inline script and add a second msg.add_attachment(...) call to the top-level message after constructing the alternatives; test the resulting MIME tree with the clients your audience uses.
SMTP security, authentication and provider differences
STARTTLS on a submission port
The first script connects with smtplib.SMTP, advertises capabilities with ehlo(), upgrades the connection with starttls(context=ssl.create_default_context()), then issues ehlo() again. Commands sent after the upgrade are encrypted. This sequence follows the documented smtplib behavior.
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Implicit TLS or another provider mode
Some providers document an implicit-TLS endpoint rather than STARTTLS. In that case, use the provider’s specified secure connection class and port instead of blindly applying the example. Do not disable certificate verification to “fix” a connection error; correct the hostname, port or trust configuration.
Login policy
smtp.login() tries authentication methods advertised by the server. A rejected login can mean incorrect credentials, a disallowed password, a required app password, OAuth-only access, an unverified sender, or an account policy that blocks SMTP. Follow the provider’s current SMTP/OAuth instructions rather than assuming a normal web-account password will work.
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- Use the actual subtype:
image/png,image/jpeg,image/gifand so on. The script detects it from the filename withmimetypes.guess_type(); an unusual extension may require an explicit mapping. - Read binary data with
read_bytes()oropen(..., "rb"). Text mode can corrupt an image. - Large images increase MIME size and may hit provider message limits. Resize or compress before sending when the recipient does not need the original resolution.
- Keep meaningful
alttext. Some clients block images or show only the plain-text alternative. - Do not promise identical layout across clients. HTML/CSS support, automatic image blocking, CID handling and attachment presentation vary; send a test to the clients your users actually use.
- Never put secrets, tokens or private data in image URLs or filenames. A CID image is embedded, but the message itself can still be forwarded or archived.
Common failures and fixes
| Symptom | Likely cause | Fix |
|---|---|---|
| Broken image icon | The HTML CID does not match the image part, or the image was added outside the related section. | Use one make_msgid() value, put image_cid[1:-1] in HTML, pass the full value to add_related(cid=...), and call it on the HTML part. |
| “Could not determine MIME type” | The filename extension is unknown or missing. | Use a recognized extension or set the known maintype and subtype explicitly after verifying the file format. |
| Authentication rejected | Wrong credentials, blocked basic password, missing app password/OAuth, or account policy. | Check the provider’s current authentication requirements and confirm the sender is permitted. |
| TLS or certificate error | Wrong host/port, implicit TLS used where STARTTLS is expected, or an invalid certificate chain. | Copy the provider’s documented endpoint, use the matching SMTP class, and keep the default SSL context. |
| Message accepted but never arrives | Provider quota, spam filtering, sender verification or recipient-side filtering. | Inspect SMTP response logs and provider activity, verify addresses, and test a small message without the image. |
| Script hangs | Network or server delay. | Set a finite SMTP timeout, as shown, and log which stage (connect, TLS, login or send) is slow. |
Testing and operational practices
- Construct the message in a local test and inspect
msg.as_string()without sending secrets to a log. - Send first to an account you control. Check an HTML-capable client, a text-only view and the attachment list.
- Test the exact image formats and sizes your application accepts.
- Keep SMTP connections short for occasional mail. For batches, follow the provider’s connection, rate and quota guidance; avoid opening an unbounded number of simultaneous sessions.
- Catch and record exception types such as
SMTPAuthenticationError,SMTPConnectErrorandSMTPServerDisconnectedwithout recording passwords or full message contents.
The standard library does not provide delivery tracking. An accepted SMTP submission means the server accepted responsibility for processing, not that the recipient read the message. Provider logs and bounce messages are the appropriate source for later delivery diagnosis.
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Or skip the browser setup
If the image you want to email is a webpage capture, you can generate it without writing browser automation. ScreenshotNeo is a screenshot API and MCP server. One GET request returns PNG, JPEG, WebP or PDF; it accepts consent banners as a visitor and removes more than 60 known consent platforms, newsletter popups and chat widgets before capture. Bot checks, blank pages, timeouts, failed loads and cache hits are not billed, and response headers identify the page verdict and billing result.
After saving the returned bytes, pass the file path to either Python email example above. The API call itself can be made with cURL:
curl -G "https://api.screenshotneo.com/v1/shot" -d access_key=YOUR_API_KEY --data-urlencode url=https://stripe.com -o shot.webpPython and Node.js equivalents are useful when capture and email are in the same job:
import requests
r = requests.get("https://api.screenshotneo.com/v1/shot", params={"access_key": "YOUR_API_KEY", "url": "https://stripe.com"}, timeout=90)
r.raise_for_status()
open("shot.webp", "wb").write(r.content)const q = new URLSearchParams({ access_key: 'YOUR_API_KEY', url: 'https://stripe.com' });
const res = await fetch(`https://api.screenshotneo.com/v1/shot?${q}`);
if (!res.ok) throw new Error(`Screenshot failed: ${res.status}`);
const image = Buffer.from(await res.arrayBuffer());See the ScreenshotNeo documentation for request options. Its MCP server includes take_screenshot, get_page_info and capture_pdf for Claude, Cursor and other MCP clients. Every plan includes all features; 1,000 screenshots per month are free with no card, and paid plans start at $5 for 3,000 shots. Create a free ScreenshotNeo account to try it.
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Frequently asked questions
Can I send an image without HTML?
Yes. Use add_attachment() with a plain-text message. HTML and Content-ID are needed only for an image displayed inside the message.
Why remove the angle brackets from the CID in HTML?
MIME headers use the bracketed Content-ID syntax, while a cid: URL uses the identifier itself. The two forms refer to the same ID.
Do I need Pillow or another image library?
No. For reading and attaching existing files, Python’s standard library is sufficient. An image library is only needed if your application must resize, convert or edit pixels.
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Frequently Asked Questions
Can I send an image without HTML?
Yes. Use add_attachment() with a plain-text message. HTML and Content-ID are needed only for an image displayed inside the message.
Why remove the angle brackets from the CID in HTML?
MIME headers use the bracketed Content-ID syntax, while a cid: URL uses the identifier itself. The two forms refer to the same ID.
Do I need Pillow or another image library?
No. For reading and attaching existing files, Python’s standard library is sufficient. An image library is only needed if your application must resize, convert or edit pixels.
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