Unfortunately that's not the case. With the gmail-base policy enabled IMAP in Outlook works and, for example: C:\Program Files\Git\usr\bin>openssl.exe s_client -connect imap.gmail.com:993
CONNECTED(00000004)
depth=2 OU = GlobalSign Root CA - R2, O = GlobalSign, CN = GlobalSign
verify return:1
depth=1 C = US, O = Google Trust Services, CN = GTS CA 1O1
verify return:1
depth=0 C = US, ST = California, L = Mountain View, O = Google LLC, CN = imap.gmail.com
verify return:1
---
Certificate chain
0 s:C = US, ST = California, L = Mountain View, O = Google LLC, CN = imap.gmail.com
i:C = US, O = Google Trust Services, CN = GTS CA 1O1
1 s:C = US, O = Google Trust Services, CN = GTS CA 1O1
i:OU = GlobalSign Root CA - R2, O = GlobalSign, CN = GlobalSign
---
Server certificate
-----BEGIN CERTIFICATE-----
MIIExjCCA66gAwIBAgIQPWEmwAUPba0FAAAAAIfqPjANBgkqhkiG9w0BAQsFADBC
MQswCQYDVQQGEwJVUzEeMBwGA1UEChMVR29vZ2xlIFRydXN0IFNlcnZpY2VzMRMw
EQYDVQQDEwpHVFMgQ0EgMU8xMB4XDTIxMDYwNzAzMDUwNloXDTIxMDgzMDAzMDUw
NVowaDELMAkGA1UEBhMCVVMxEzARBgNVBAgTCkNhbGlmb3JuaWExFjAUBgNVBAcT
DU1vdW50YWluIFZpZXcxEzARBgNVBAoTCkdvb2dsZSBMTEMxFzAVBgNVBAMTDmlt
etc..... With the gmail-base policy disabled IMAP in Outlook fails and: C:\Program Files\Git\usr\bin>openssl.exe s_client -connect imap.gmail.com:993
CONNECTED(00000004)
write:errno=104
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 0 bytes and written 316 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
--- Enable the policy and it's working again. I went through and instead of taking a bunch of screenshots, here are the two policies: inside to outside policy:
source: inside any
user: any any
destination: outside any
application: any
service/url: application-default any
actions: allow, various profile lists
allow gmail imap etc policy:
source: inside any
user: any any
destination: outside any
application: gmail-base
service/url: application-default any
actions: allow, various profile lists (identical to other policy) I don't understand why adding a more restrictive policy allows an application to work.
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