I tried to connect to Gmail successfully using the following (after allowing Less secure app access in Gmail):

server=MailServerConnect[
    "imap.gmail.com",
    MailSettings-><|
        "Username"->"xxx@gmail.com",
        "Password"->"xxx",
        "PortNumber"->Automatic
    |>
]

And have been able to manage it from Mathematica, but can't get it to connect to my Hotmail account.

I got the following setting from my account:

POP setting:

Server name: outlook.office365.com Port: 995 Encryption method: TLS

IMAP setting:

Server name: outlook.office365.com Port: 993 Encryption method: TLS

SMTP setting:

Server name: smtp.office365.com Port: 587 Encryption method: STARTTLS

Based on that I tried the following command:

server=MailServerConnect[
    "outlook.office365.com",
    MailSettings-><|
        "Username"->"xxx@hotmail.com",
        "Password"->"xxx",
        "PortNumber"->993,
        "EncryptionProtocol"->"TLS"
    |>
];
folder=serverHotmail["Inbox"];
item=folder[-1]

output is:

$Failed

The data is completely empty unlike the Google one. So why is it not working?