I am having major issues with Outlook and Office365. Mail is sitting in my outbox and not sending. This only started to happen after I had implemented a VLAN infrastructure at my office.
I have setup multiple VLAN's in my office. My servers and workstations are on one VLAN and other VLAN's for other server hosting purposes, such as backups and voice.
HP1820 - SW 1 is connected to SW 2 via VLAN trunk
HP1820 - SW 2 has a connection from SW 1 and has the extra VLAN trunk to the Draytek 2952
HP1820 PoE - SW3 directly connected via VLAN trunk to the Draytek 2952
I have 3 HP 1820 switches and 1 of them is a PoE (SW3). The PoE's sole purpose is for VoiP and is directly connected to my Draytek 2952 via tagged port on the switch. All is working fine.
The other 2 HP 1820's are for the main network and i have around 5 VLAN's setup. SW1 and SW2 are connected via Port #24 via a VLAN Trunk.
On SW2 port #23 is connected to the Draytek via VLAN trunk also.
All VLAN connections have internet and able to communicate internally as well out.
I have one major big issue with Outlook. My mail is stuck and i have captured some Wireshark TCP captures.
Can someone please help me as i am baffled and confused as to why this is happening only with the connection to Office365.