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I'm trying to get my SSL certificate to work with Exchange 2010 but it's not working on chrome... The server is running the updated to the latest version. Rollup update 23. The SSL cert is self-signed using a 2-tier PKI

CPU: AMD Ryzen 5 5600X | CPU Cooler: Stock AMD Cooler | Motherboard: Asus ROG STRIX B550-F GAMING (WI-FI) | RAM: Corsair Vengeance LPX 32 GB (4x 8 GB) DDR4-3000 CL16 | GPU: Nvidia GTX 1060 6GB Zotac Mini | Case: K280 Case | PSU: Cooler Master B600 Power supply | SSD: 1TB  | HDDs: 1x 250GB & 1x 1TB WD Blue | Monitor: 24" Acer S240HLBID | OS: Win 11 Pro.

 

Home Lab:  Lenovo ThinkCenter M82 Hyper-V Server 2022 | Dell OptiPlex 9020 Hyper-V Server 2022 | TP-LINK TL-SG108E | Cisco Catalyst C2960CG 8 Port Switch | HP MicroServer G8 SCCM Server | 2x Dell PowerEdge R630 Hyper-V Server 2022

 

 

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23 minutes ago, unijab said:

Your clients must install the signing CAs certificate if you don't want to be prompted any more.

everything is installed... :/ 

CPU: AMD Ryzen 5 5600X | CPU Cooler: Stock AMD Cooler | Motherboard: Asus ROG STRIX B550-F GAMING (WI-FI) | RAM: Corsair Vengeance LPX 32 GB (4x 8 GB) DDR4-3000 CL16 | GPU: Nvidia GTX 1060 6GB Zotac Mini | Case: K280 Case | PSU: Cooler Master B600 Power supply | SSD: 1TB  | HDDs: 1x 250GB & 1x 1TB WD Blue | Monitor: 24" Acer S240HLBID | OS: Win 11 Pro.

 

Home Lab:  Lenovo ThinkCenter M82 Hyper-V Server 2022 | Dell OptiPlex 9020 Hyper-V Server 2022 | TP-LINK TL-SG108E | Cisco Catalyst C2960CG 8 Port Switch | HP MicroServer G8 SCCM Server | 2x Dell PowerEdge R630 Hyper-V Server 2022

 

 

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How about make a valid cert from Let's Encrypt? It is not so complicated and works very well (I running this personally on Exchange 2010 On-Prem). The only issue is you must update IIS to 8 in order to autorenewal to work(or just renew cert manually every 2-3 mounts).

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1 hour ago, kbelyhk said:

How about make a valid cert from Let's Encrypt? It is not so complicated and works very well (I running this personally on Exchange 2010 On-Prem). The only issue is you must update IIS to 8 in order to autorenewal to work(or just renew cert manually every 2-3 mounts).

I already have an SSL for outside OWA. We need one for internal use. 

CPU: AMD Ryzen 5 5600X | CPU Cooler: Stock AMD Cooler | Motherboard: Asus ROG STRIX B550-F GAMING (WI-FI) | RAM: Corsair Vengeance LPX 32 GB (4x 8 GB) DDR4-3000 CL16 | GPU: Nvidia GTX 1060 6GB Zotac Mini | Case: K280 Case | PSU: Cooler Master B600 Power supply | SSD: 1TB  | HDDs: 1x 250GB & 1x 1TB WD Blue | Monitor: 24" Acer S240HLBID | OS: Win 11 Pro.

 

Home Lab:  Lenovo ThinkCenter M82 Hyper-V Server 2022 | Dell OptiPlex 9020 Hyper-V Server 2022 | TP-LINK TL-SG108E | Cisco Catalyst C2960CG 8 Port Switch | HP MicroServer G8 SCCM Server | 2x Dell PowerEdge R630 Hyper-V Server 2022

 

 

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3 hours ago, leadeater said:

Post a screen shot of the certain chain from the chrome browser

I ended changing the OS from 2012 to 2016. Everything is working fine. :) 

CPU: AMD Ryzen 5 5600X | CPU Cooler: Stock AMD Cooler | Motherboard: Asus ROG STRIX B550-F GAMING (WI-FI) | RAM: Corsair Vengeance LPX 32 GB (4x 8 GB) DDR4-3000 CL16 | GPU: Nvidia GTX 1060 6GB Zotac Mini | Case: K280 Case | PSU: Cooler Master B600 Power supply | SSD: 1TB  | HDDs: 1x 250GB & 1x 1TB WD Blue | Monitor: 24" Acer S240HLBID | OS: Win 11 Pro.

 

Home Lab:  Lenovo ThinkCenter M82 Hyper-V Server 2022 | Dell OptiPlex 9020 Hyper-V Server 2022 | TP-LINK TL-SG108E | Cisco Catalyst C2960CG 8 Port Switch | HP MicroServer G8 SCCM Server | 2x Dell PowerEdge R630 Hyper-V Server 2022

 

 

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