Emails are breaking went sent to a gmail addresss - email

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.

Related

MS Graph: Mail with large attachmnet is rejected by recepient

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.

Few cases are not getting created in Email-To-Case(With attachment)

I sent an email with an attachment from my mail(outlook and Gmail) account to the email address which is routed in my org and the case(with attachment) got created in salesforce org.
Here the issue is, it is working good sometimes and not working sometimes. I sent an email from multiple personal email IDs and I am facing the same issue. How to fix or debug this?

SendGrid smtp not sending to Yahoo, AOL, or Verizon.net but sends to Gmail?

(Disclaimer I'm fairly new to development in general and this is my first StackOverflow post all and any feedback is greatly appreciated.)
I'm posting here because I'm on a free SendGrid account and their support team has yet to get back to respond and it's been over a week and I'm dying to solve this issue.
Currently, I'm using Sendgrid as an SMTP and recently my emails have stopped sending to the following esp Yahoo, AOL, and Verizon.net but emails send to Gmail just fine.
Because emails still send to Gmail I used "Email Header Analyzer" via mxtoolbox.com to review and meet the recommendations provided. Which I have implemented on. (See screenshot)
The only thing not checked off is the "DKIM Authenticated" in which it's my understanding that when you verify the domain you're using to send emails with SendGrid takes care of that for you.
It's not the email function itself because it sends just fine to Gmail.
My question is has anyone else experienced this issue? If so what was the fix you did that made it work?
Screenshot of my email header analyzer results:
Turns out that my SendGrid account was over the daily email sending limit for the "free plan" and the emails that were sent correctly to Gmail had been doing so because of a pre-existing mail function (not using SendGrid even though SendGrid was still logging these emails).
I figured out this was happening by looking at the "mailed-by:" info when you toggle the drop-down above the email just under the sender email address. Mailed-ByView With SendGrid it would say "mail-by: sendgird.net" SendGird-Mailed-ByView
It would have been nice if SendGrid made my sending limit information a little more apparent but you can find this information about your account by going to "Settings">"Account Details">"Your Products." YourProductsView

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.

Email received sent via webmail but not Javamail

I'm trying to send emails via Javamail to a corporate account. My Java test app works fine when I send message to gmail and my personal email. I can also successfully send to the corporate account via my email hosting webmail client.
I've read through posts here and have tried setting -Djava.net.preferIPv4Stack=true in the VM for the test app but it did not work.
I have checked the junk mail at the corporate client and the message is not there. That is not to say its not being blocked elsewhere at the corporate site.
Any ideas what can be causing this problem?
I'm using org.apache.commons.mail.HmtlEmail and this is the test code:
// Create the email message
HtmlEmail email = new HtmlEmail();
email.setHostName(smtpHost);
email.setAuthenticator(new DefaultAuthenticator(smtpUser, smtpPwd));
email.setSSLOnConnect(true);
email.addTo(to);
email.setFrom(from);
email.setSubject(subject);
// set the html message
email.setHtmlMsg(text);
// set the alternative message
email.setTextMsg("Your email client does not support HTML messages");
// send the email
email.send();
So #Bill's question regarding Javamail debug output got me thinking about the content of the email message. The debug log shows all is fine but what I found was I included Bootstrap and Fontawsome JS / CSS links in the email header and that caused the message to be rejected by the corporate system for security reasons presumably. Thanks for the help