diff --git a/coderd/azureidentity/azureidentity.go b/coderd/azureidentity/azureidentity.go
index c1c766bcc9..e4da9e54fc 100644
--- a/coderd/azureidentity/azureidentity.go
+++ b/coderd/azureidentity/azureidentity.go
@@ -122,69 +122,91 @@ func Validate(ctx context.Context, signature string, options Options) (string, e
 // 2. Convert to PEM format: `openssl x509 -in cert.pem -text`
 // 3. Paste the contents into the array below
 var Certificates = []string{
-	// Microsoft RSA TLS CA 01
+	// Microsoft Azure ECC TLS Issuing CA 03
 	`-----BEGIN CERTIFICATE-----
-MIIFWjCCBEKgAwIBAgIQDxSWXyAgaZlP1ceseIlB4jANBgkqhkiG9w0BAQsFADBa
-MQswCQYDVQQGEwJJRTESMBAGA1UEChMJQmFsdGltb3JlMRMwEQYDVQQLEwpDeWJl
-clRydXN0MSIwIAYDVQQDExlCYWx0aW1vcmUgQ3liZXJUcnVzdCBSb290MB4XDTIw
-MDcyMTIzMDAwMFoXDTI0MTAwODA3MDAwMFowTzELMAkGA1UEBhMCVVMxHjAcBgNV
-BAoTFU1pY3Jvc29mdCBDb3Jwb3JhdGlvbjEgMB4GA1UEAxMXTWljcm9zb2Z0IFJT
-QSBUTFMgQ0EgMDEwggIiMA0GCSqGSIb3DQEBAQUAA4ICDwAwggIKAoICAQCqYnfP
-mmOyBoTzkDb0mfMUUavqlQo7Rgb9EUEf/lsGWMk4bgj8T0RIzTqk970eouKVuL5R
-IMW/snBjXXgMQ8ApzWRJCZbar879BV8rKpHoAW4uGJssnNABf2n17j9TiFy6BWy+
-IhVnFILyLNK+W2M3zK9gheiWa2uACKhuvgCca5Vw/OQYErEdG7LBEzFnMzTmJcli
-W1iCdXby/vI/OxbfqkKD4zJtm45DJvC9Dh+hpzqvLMiK5uo/+aXSJY+SqhoIEpz+
-rErHw+uAlKuHFtEjSeeku8eR3+Z5ND9BSqc6JtLqb0bjOHPm5dSRrgt4nnil75bj
-c9j3lWXpBb9PXP9Sp/nPCK+nTQmZwHGjUnqlO9ebAVQD47ZisFonnDAmjrZNVqEX
-F3p7laEHrFMxttYuD81BdOzxAbL9Rb/8MeFGQjE2Qx65qgVfhH+RsYuuD9dUw/3w
-ZAhq05yO6nk07AM9c+AbNtRoEcdZcLCHfMDcbkXKNs5DJncCqXAN6LhXVERCw/us
-G2MmCMLSIx9/kwt8bwhUmitOXc6fpT7SmFvRAtvxg84wUkg4Y/Gx++0j0z6StSeN
-0EJz150jaHG6WV4HUqaWTb98Tm90IgXAU4AW2GBOlzFPiU5IY9jt+eXC2Q6yC/Zp
-TL1LAcnL3Qa/OgLrHN0wiw1KFGD51WRPQ0Sh7QIDAQABo4IBJTCCASEwHQYDVR0O
-BBYEFLV2DDARzseSQk1Mx1wsyKkM6AtkMB8GA1UdIwQYMBaAFOWdWTCCR1jMrPoI
-VDaGezq1BE3wMA4GA1UdDwEB/wQEAwIBhjAdBgNVHSUEFjAUBggrBgEFBQcDAQYI
-KwYBBQUHAwIwEgYDVR0TAQH/BAgwBgEB/wIBADA0BggrBgEFBQcBAQQoMCYwJAYI
-KwYBBQUHMAGGGGh0dHA6Ly9vY3NwLmRpZ2ljZXJ0LmNvbTA6BgNVHR8EMzAxMC+g
-LaArhilodHRwOi8vY3JsMy5kaWdpY2VydC5jb20vT21uaXJvb3QyMDI1LmNybDAq
-BgNVHSAEIzAhMAgGBmeBDAECATAIBgZngQwBAgIwCwYJKwYBBAGCNyoBMA0GCSqG
-SIb3DQEBCwUAA4IBAQCfK76SZ1vae4qt6P+dTQUO7bYNFUHR5hXcA2D59CJWnEj5
-na7aKzyowKvQupW4yMH9fGNxtsh6iJswRqOOfZYC4/giBO/gNsBvwr8uDW7t1nYo
-DYGHPpvnpxCM2mYfQFHq576/TmeYu1RZY29C4w8xYBlkAA8mDJfRhMCmehk7cN5F
-JtyWRj2cZj/hOoI45TYDBChXpOlLZKIYiG1giY16vhCRi6zmPzEwv+tk156N6cGS
-Vm44jTQ/rs1sa0JSYjzUaYngoFdZC4OfxnIkQvUIA4TOFmPzNPEFdjcZsgbeEz4T
-cGHTBPK4R28F44qIMCtHRV55VMX53ev6P3hRddJb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 -----END CERTIFICATE-----`,
-	// Microsoft RSA TLS CA 02
+	// Microsoft Azure ECC TLS Issuing CA 04
 	`-----BEGIN CERTIFICATE-----
-MIIFWjCCBEKgAwIBAgIQD6dHIsU9iMgPWJ77H51KOjANBgkqhkiG9w0BAQsFADBa
-MQswCQYDVQQGEwJJRTESMBAGA1UEChMJQmFsdGltb3JlMRMwEQYDVQQLEwpDeWJl
-clRydXN0MSIwIAYDVQQDExlCYWx0aW1vcmUgQ3liZXJUcnVzdCBSb290MB4XDTIw
-MDcyMTIzMDAwMFoXDTI0MTAwODA3MDAwMFowTzELMAkGA1UEBhMCVVMxHjAcBgNV
-BAoTFU1pY3Jvc29mdCBDb3Jwb3JhdGlvbjEgMB4GA1UEAxMXTWljcm9zb2Z0IFJT
-QSBUTFMgQ0EgMDIwggIiMA0GCSqGSIb3DQEBAQUAA4ICDwAwggIKAoICAQD0wBlZ
-qiokfAYhMdHuEvWBapTj9tFKL+NdsS4pFDi8zJVdKQfR+F039CDXtD9YOnqS7o88
-+isKcgOeQNTri472mPnn8N3vPCX0bDOEVk+nkZNIBA3zApvGGg/40Thv78kAlxib
-MipsKahdbuoHByOB4ZlYotcBhf/ObUf65kCRfXMRQqOKWkZLkilPPn3zkYM5GHxe
-I4MNZ1SoKBEoHa2E/uDwBQVxadY4SRZWFxMd7ARyI4Cz1ik4N2Z6ALD3MfjAgEED
-woknyw9TGvr4PubAZdqU511zNLBoavar2OAVTl0Tddj+RAhbnX1/zypqk+ifv+d3
-CgiDa8Mbvo1u2Q8nuUBrKVUmR6EjkV/dDrIsUaU643v/Wp/uE7xLDdhC5rplK9si
-NlYohMTMKLAkjxVeWBWbQj7REickISpc+yowi3yUrO5lCgNAKrCNYw+wAfAvhFkO
-eqPm6kP41IHVXVtGNC/UogcdiKUiR/N59IfYB+o2v54GMW+ubSC3BohLFbho/oZZ
-5XyulIZK75pwTHmauCIeE5clU9ivpLwPTx9b0Vno9+ApElrFgdY0/YKZ46GfjOC9
-ta4G25VJ1WKsMmWLtzyrfgwbYopquZd724fFdpvsxfIvMG5m3VFkThOqzsOttDcU
-fyMTqM2pan4txG58uxNJ0MjR03UCEULRU+qMnwIDAQABo4IBJTCCASEwHQYDVR0O
-BBYEFP8vf+EG9DjzLe0ljZjC/g72bPz6MB8GA1UdIwQYMBaAFOWdWTCCR1jMrPoI
-VDaGezq1BE3wMA4GA1UdDwEB/wQEAwIBhjAdBgNVHSUEFjAUBggrBgEFBQcDAQYI
-KwYBBQUHAwIwEgYDVR0TAQH/BAgwBgEB/wIBADA0BggrBgEFBQcBAQQoMCYwJAYI
-KwYBBQUHMAGGGGh0dHA6Ly9vY3NwLmRpZ2ljZXJ0LmNvbTA6BgNVHR8EMzAxMC+g
-LaArhilodHRwOi8vY3JsMy5kaWdpY2VydC5jb20vT21uaXJvb3QyMDI1LmNybDAq
-BgNVHSAEIzAhMAgGBmeBDAECATAIBgZngQwBAgIwCwYJKwYBBAGCNyoBMA0GCSqG
-SIb3DQEBCwUAA4IBAQCg2d165dQ1tHS0IN83uOi4S5heLhsx+zXIOwtxnvwCWdOJ
-3wFLQaFDcgaMtN79UjMIFVIUedDZBsvalKnx+6l2tM/VH4YAyNPx+u1LFR0joPYp
-QYLbNYkedkNuhRmEBesPqj4aDz68ZDI6fJ92sj2q18QvJUJ5Qz728AvtFOat+Ajg
-K0PFqPYEAviUKr162NB1XZJxf6uyIjUlnG4UEdHfUqdhl0R84mMtrYINksTzQ2sH
-YM8fEhqICtTlcRLr/FErUaPUe9648nziSnA0qKH7rUZqP/Ifmbo+WNZSZG1BbgOh
-lk+521W+Ncih3HRbvRBE0LWYT8vWKnfjgZKxwHwJ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-----END CERTIFICATE-----`,
+	// Microsoft Azure ECC TLS Issuing CA 07
+	`-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----`,
+	// Microsoft Azure ECC TLS Issuing CA 08
+	`-----BEGIN CERTIFICATE-----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 -----END CERTIFICATE-----`,
 	// Microsoft Azure RSA TLS Issuing CA 03
 	`-----BEGIN CERTIFICATE-----
@@ -321,6 +343,70 @@ ixFJEOcAMKKR55mSC5W4nQ6jDfp7Qy/504MQpdjJflk90RHsIZGXVPw/JdbBp0w6
 pDb4o5CqydmZqZMrEvbGk1p8kegFkBekp/5WVfd86BdH2xs+GKO3hyiA8iBrBCGJ
 fqrijbRnZm7q5+ydXF3jhJDJWfxW5EBYZBJrUz/a+8K/78BjwI8z2VYJpG4t6r4o
 tOGB5sEyDPDwqx00Rouu8g==
+-----END CERTIFICATE-----`,
+	// Microsoft RSA TLS CA 01
+	`-----BEGIN CERTIFICATE-----
+MIIFWjCCBEKgAwIBAgIQDxSWXyAgaZlP1ceseIlB4jANBgkqhkiG9w0BAQsFADBa
+MQswCQYDVQQGEwJJRTESMBAGA1UEChMJQmFsdGltb3JlMRMwEQYDVQQLEwpDeWJl
+clRydXN0MSIwIAYDVQQDExlCYWx0aW1vcmUgQ3liZXJUcnVzdCBSb290MB4XDTIw
+MDcyMTIzMDAwMFoXDTI0MTAwODA3MDAwMFowTzELMAkGA1UEBhMCVVMxHjAcBgNV
+BAoTFU1pY3Jvc29mdCBDb3Jwb3JhdGlvbjEgMB4GA1UEAxMXTWljcm9zb2Z0IFJT
+QSBUTFMgQ0EgMDEwggIiMA0GCSqGSIb3DQEBAQUAA4ICDwAwggIKAoICAQCqYnfP
+mmOyBoTzkDb0mfMUUavqlQo7Rgb9EUEf/lsGWMk4bgj8T0RIzTqk970eouKVuL5R
+IMW/snBjXXgMQ8ApzWRJCZbar879BV8rKpHoAW4uGJssnNABf2n17j9TiFy6BWy+
+IhVnFILyLNK+W2M3zK9gheiWa2uACKhuvgCca5Vw/OQYErEdG7LBEzFnMzTmJcli
+W1iCdXby/vI/OxbfqkKD4zJtm45DJvC9Dh+hpzqvLMiK5uo/+aXSJY+SqhoIEpz+
+rErHw+uAlKuHFtEjSeeku8eR3+Z5ND9BSqc6JtLqb0bjOHPm5dSRrgt4nnil75bj
+c9j3lWXpBb9PXP9Sp/nPCK+nTQmZwHGjUnqlO9ebAVQD47ZisFonnDAmjrZNVqEX
+F3p7laEHrFMxttYuD81BdOzxAbL9Rb/8MeFGQjE2Qx65qgVfhH+RsYuuD9dUw/3w
+ZAhq05yO6nk07AM9c+AbNtRoEcdZcLCHfMDcbkXKNs5DJncCqXAN6LhXVERCw/us
+G2MmCMLSIx9/kwt8bwhUmitOXc6fpT7SmFvRAtvxg84wUkg4Y/Gx++0j0z6StSeN
+0EJz150jaHG6WV4HUqaWTb98Tm90IgXAU4AW2GBOlzFPiU5IY9jt+eXC2Q6yC/Zp
+TL1LAcnL3Qa/OgLrHN0wiw1KFGD51WRPQ0Sh7QIDAQABo4IBJTCCASEwHQYDVR0O
+BBYEFLV2DDARzseSQk1Mx1wsyKkM6AtkMB8GA1UdIwQYMBaAFOWdWTCCR1jMrPoI
+VDaGezq1BE3wMA4GA1UdDwEB/wQEAwIBhjAdBgNVHSUEFjAUBggrBgEFBQcDAQYI
+KwYBBQUHAwIwEgYDVR0TAQH/BAgwBgEB/wIBADA0BggrBgEFBQcBAQQoMCYwJAYI
+KwYBBQUHMAGGGGh0dHA6Ly9vY3NwLmRpZ2ljZXJ0LmNvbTA6BgNVHR8EMzAxMC+g
+LaArhilodHRwOi8vY3JsMy5kaWdpY2VydC5jb20vT21uaXJvb3QyMDI1LmNybDAq
+BgNVHSAEIzAhMAgGBmeBDAECATAIBgZngQwBAgIwCwYJKwYBBAGCNyoBMA0GCSqG
+SIb3DQEBCwUAA4IBAQCfK76SZ1vae4qt6P+dTQUO7bYNFUHR5hXcA2D59CJWnEj5
+na7aKzyowKvQupW4yMH9fGNxtsh6iJswRqOOfZYC4/giBO/gNsBvwr8uDW7t1nYo
+DYGHPpvnpxCM2mYfQFHq576/TmeYu1RZY29C4w8xYBlkAA8mDJfRhMCmehk7cN5F
+JtyWRj2cZj/hOoI45TYDBChXpOlLZKIYiG1giY16vhCRi6zmPzEwv+tk156N6cGS
+Vm44jTQ/rs1sa0JSYjzUaYngoFdZC4OfxnIkQvUIA4TOFmPzNPEFdjcZsgbeEz4T
+cGHTBPK4R28F44qIMCtHRV55VMX53ev6P3hRddJb
+-----END CERTIFICATE-----`,
+	// Microsoft RSA TLS CA 02
+	`-----BEGIN CERTIFICATE-----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 -----END CERTIFICATE-----`,
 	// Microsoft Azure TLS Issuing CA 01
 	`-----BEGIN CERTIFICATE-----
diff --git a/coderd/azureidentity/generate.sh b/coderd/azureidentity/generate.sh
index 8d8973259a..e181a842d0 100755
--- a/coderd/azureidentity/generate.sh
+++ b/coderd/azureidentity/generate.sh
@@ -1,13 +1,21 @@
 #!/usr/bin/env bash
 
-# See: https://learn.microsoft.com/en-us/azure/security/fundamentals/azure-ca-details?tabs=certificate-authority-chains
+# Add the cross-sign issuing certificates from the subordinate certificate
+# authorities.
+# See: https://learn.microsoft.com/en-us/azure/security/fundamentals/azure-ca-details
 declare -a CERTIFICATES=(
-	"Microsoft RSA TLS CA 01=https://crt.sh/?d=3124375355"
-	"Microsoft RSA TLS CA 02=https://crt.sh/?d=3124375356"
+	"Microsoft Azure ECC TLS Issuing CA 03=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20ECC%20TLS%20Issuing%20CA%2003%20-%20xsign.crt"
+	"Microsoft Azure ECC TLS Issuing CA 04=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20ECC%20TLS%20Issuing%20CA%2004%20-%20xsign.crt"
+	"Microsoft Azure ECC TLS Issuing CA 07=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20ECC%20TLS%20Issuing%20CA%2007%20-%20xsign.crt"
+	"Microsoft Azure ECC TLS Issuing CA 08=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20ECC%20TLS%20Issuing%20CA%2008%20-%20xsign.crt"
 	"Microsoft Azure RSA TLS Issuing CA 03=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20RSA%20TLS%20Issuing%20CA%2003%20-%20xsign.crt"
 	"Microsoft Azure RSA TLS Issuing CA 04=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20RSA%20TLS%20Issuing%20CA%2004%20-%20xsign.crt"
 	"Microsoft Azure RSA TLS Issuing CA 07=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20RSA%20TLS%20Issuing%20CA%2007%20-%20xsign.crt"
 	"Microsoft Azure RSA TLS Issuing CA 08=https://www.microsoft.com/pkiops/certs/Microsoft%20Azure%20RSA%20TLS%20Issuing%20CA%2008%20-%20xsign.crt"
+
+	# These have expired, but leaving them in for now.
+	"Microsoft RSA TLS CA 01=https://crt.sh/?d=3124375355"
+	"Microsoft RSA TLS CA 02=https://crt.sh/?d=3124375356"
 	"Microsoft Azure TLS Issuing CA 01=https://www.microsoft.com/pki/certs/Microsoft%20Azure%20TLS%20Issuing%20CA%2001.cer"
 	"Microsoft Azure TLS Issuing CA 02=https://www.microsoft.com/pki/certs/Microsoft%20Azure%20TLS%20Issuing%20CA%2002.cer"
 	"Microsoft Azure TLS Issuing CA 05=https://www.microsoft.com/pki/certs/Microsoft%20Azure%20TLS%20Issuing%20CA%2005.cer"