Recently my Kasperksy VPN IP addresse range has been blocked by Microsoft Endpoint protection uses the SPAMHaus.org list, which blocked Kaspersky's address ranges.
Here's how to check if your VPN blocks your connectivity to your mail server.
1) Run Cmd.exe
2) Issue nslookup (while command while connected with your vpn)
3) Type set type = mx (we going to find the mail server record (mx) for this url)
4) Use domain for you email address (metadataconsulting@outlook.com) domain is outlook.com
Type outlook.com
C:\>nslookup Default Server: dns.google Address: 8.8.8.8 > set type=mx > outlook.com Server: dns.google Address: 8.8.8.8 Non-authoritative answer: outlook.com MX preference = 5, mail exchanger = outlook-com.olc.protection.outlook.com >
4) Grab mail exchanger value "outlook-com.olc.protection.outlook.com",
this is your SMTP (Simple Mail Transfer Protocol) server address for outlook.com.
For Outlook, aliases are also addresses are outlook.office365.com, outlook.ha.office365.com etc.
5) Exit (Ctrl-c)
6) ping outlook-com.olc.protection.outlook.com
Pinging outlook-com.olc.protection.outlook.com [104.47.55.33] with 32 bytes of data: Request timed out. Request timed out. Request timed out. Request timed out. Ping statistics for 104.47.55.33: Packets: Sent = 4, Received = 0, Lost = 4 (100% loss), Non-authoritative answer: outlook.com MX preference = 5, mail exchanger = outlook-com.olc.protection.outlook.com >
Well, let's try with telnet to test this SMTP server, on standard SMTP port 25.
This is standard way administrators use to test their mail servers.
7) Issue telnet outlook-com.olc.protection.outlook.com 25
Returns he its back.....okay we are in
220 DM6NAM10FT023.mail.protection.outlook.com Microsoft ESMTP MAIL Service ready at Mon, 8 Feb 2021 20:59:11 +0000
8) Issue EHLO or HELO
EHLO metadataconsulting.ca 250-BN8NAM12FT031.mail.protection.outlook.com Hello [107.181.177.255] 250-SIZE 49283072 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-8BITMIME 250-BINARYMIME 250-CHUNKING 250 SMTPUTF8
550 5.7.1 Service unavailable, Client host [107.181.177.255] blocked using Spamhaus.
To request removal from this list see https://www.spamhaus.org/query/ip/107.181.177.255 12.prod.protection.outlook.com]
BTW a result and email address check would be return the following, this is using google mail server.
MAIL FROM from SMTP Server : 250 2.1.0 OK m22si19950956pgu.215 - gsmtp RCPT TO from SMTP Server : 250 2.1.5 OK m22si19950956pgu.215 - gsmtp
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