Hi,
I have also observed similar behavior once.
My guess is that, when you send multiple emails with the same
Date, Message-ID, and Subject [this is what I did] gmail fails to recognize
that there
is a new message on the server.

Best wishes,
Adrian

czw., 29 wrz 2022 o 08:32 jian he via curl-library <
curl-library@lists.haxx.se> napisaƂ(a):

> https://curl.se/libcurl/c/smtp-mail.html
>
> https://stackoverflow.com/questions/37092597/sending-an-email-with-libcurl-smtp-with-gmail-login-denied
>
> I use 465, so I follow the SO post instructions:
>
>> curl_easy_setopt(curl,CURLOPT_URL,"smtps://smtp.gmail.com:465");
>> //curl_easy_setopt(curl,CURLOPT_USE_SSL,CURLUSESSL_ALL);
>>
>>
> Seems you cannot run this program multi times.
> if I run *gcc -Wall -Wextra -pedantic -Wshadow -Ofast curl_stmp1.c -lcurl
> &&./a.out *
> then the second time, it won't deliver a message.
>
> I need to constantly change the subject.
> 1st time subject: SMTP example messageTEST TEST01
> 2nd time subject: SMTP example messageTEST TEST02
>
> not sure why?
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