MS Graph: Mail with large attachmnet is rejected by recepient - email

MS Graph uses different method to send attachments larger than 3MB. My code usses method .Messages[msg.Id].Attachments.Request().AddAsync(attachment); to add attachment smaller than 3MB and method Messages[msg.Id].Attachments.CreateUploadSession(attachmentItem).Request().PostAsync(); for attacments larger than 3MB. Code works fine and I see sent mails in Sent folder. When recepient is Gmail (Google workspace account), mail was rejected. If I remove large attacment (about 3.5MB), mail is received. Google documentation says that receiving message limit is 15MB.
I tried to send mail with large attachment to different recepients. If recepient is MS365 recepient, mail is delivered. Yahoo, Gmail and few tested receiving sides rejected mail.
Is there anything special in the code to make it work with other mail servers except MS365?
Edit:
I tried to send mail using OWA and same account as sender, same recipient. Mail was rejected. It seems no problem in code.

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Emails are breaking went sent to a gmail addresss

I have a unique issue. Whenever i sent email to my office account they open fine in the email client. However any email sent to Gmail has multiple issues. The CSS styling gets striped and the PDF attachments get corrupted.
I am sending my mails from the NopCommerce system and dont see any known issue of the kind in the forum.

How to reduce number of deferred emails SMTP SendGrid

I am using sendgrid to send out emails. My Django code for sending emails looks something like this
client_message = EmailMessage(
'Subject',
'Message Content',
'Name <support#domain.org>',
[client_email],
['support#domain.org],
)
client_message.content_subtype = "html"
client_message.attach('MyFile.pdf', file, 'application/pdf')
client_message.send(fail_silently=False)
I have the content_subtype as HTML so that I can do page breaks between paragraphs.
I am sending out 2 emails at a time and am sending a very low volume, < 100 / day. I just began sending emails. My emails are landing in Gmail spam inbox and not getting delivered at all into Yahoo / Comcast. I have already whitelisted my own domain's DNS using SendGrid.
What is best policy for my email content so get them delivered? I have heard
Removing all hyperlinks in my message
Putting a physical mailing address in the footer of the email
Putting the words "reply STOP to unsubscribe" in the email footer
Changing the content type of my email from HTML
It's important that I attach the files when sending the email. What else can I do to make sure my emails go through?
I had just verified my domain a few hours before sending the ultimately deferred emails. I believe the answer is that my domain verification was still being processed, and my emails landed in the the recipients inbox 2 days later. For future people having this problem, if possible see if the problem fixes itself after a few days.
Litmus.com is also a fantastic resource to check your content and security settings.

Gmail blocked emails sent from Send Grid

We are trying to send mail on to Gmail account by using send grid api but Gmail has blocked the email which is sent from send grid. Please check the message given below:
550 5.7.1 [167.89.24.147 12] Our system has detected that this message is likely unsolicited mail. To reduce the amount of spam sent to Gmail, this message has been blocked. Please visit http://support.google.com/mail/bin/answer.py?hl=en&answer=188131 for more information. kw15si11591084pab.218 - gsmtp
We have checked all header parameter suggested by Send Grid and implemented it in our code. At the same moment, it works fine for other domain like AOL, Rediff etc.
Please suggest how we overcome with this problem as we have huge users on Gmail and we will send our emails to all those users as. Also, we have noticed that the email came after some time from Send Grid.
Many thanks in advance.
The recipient mail server analyzed your message and determined that the content of the message is spammy. My recommendation would be to run your formatted message through a third-party service, www.mail-tester.com , to identify ways to improve the reception of the message. It's also possible that your sending IP address, 167.89.24.147 based on the response message you've included, is listed on a black list. You'll want to scan your sending IP on a site like http://multirbl.valli.org/ and, if you see that your IP is listed anywhere, submit a delisting request with the black list.
SendGrid also has a Spam Checker app - Turning on SendGrid's Spam Checker app can help combat this, as you're able to set a predefined filter and get alerted when your content exceeds the filter that you set.

Sending an email using javamail as if it were being sent from gmail

I'm developing a web application that uses javamail to send email messages and it works correctly.
The problem is that I don't get the email that I'm sending in the sent mail folder in the gmail account which I connect to, also I don't get bounced email as it happens if I try to send the email via gmail application.
I doubt this is due to security restrictions from javamail and cannot be done, as it would be much faster to get a possible spam list from an email server than doing it manually.but if it's for security reasons it would just be much better just not to bounce emails.
How can I use javamail as if sending the mails from gmail.com, getting the sent message in the sent mail folder and bounced mails in inbox folder?
The problem is that I don't get the email that I'm sending in the sent mail folder
Sending a mail via SMTP does not copy it to a sent folder automatically. Your sending application would have to make an IMAP connection after the SMTP connection and copy the message into the sent folder.
also I don't get bounced email
Make sure the Evelope Sender Address ("Return-Path") is set to the Gmail Adress you're using to send the messages.

Email that allows auto responses via subject line with attachments

i want to host a email client on my web server that allows messages to be processed via subject line, i looked into roundcube's autoreply but that was only a global message for all incoming emails, for example, if my customer emailed me with subject line HOSTING, it would be filtered and sent an auto response with an attached pdf file of our hosting plans
I would actually use Gmail's filters to do this, as otherwise it would be quite complicated. I would forward all the mail to Gmail, and use Gmail's filters (and canned response lab feature) to respond with the PDF attachment.