diff --git a/coderd/azureidentity/azureidentity_test.go b/coderd/azureidentity/azureidentity_test.go
index 14ca0c53ab..2c12e95aee 100644
--- a/coderd/azureidentity/azureidentity_test.go
+++ b/coderd/azureidentity/azureidentity_test.go
@@ -21,7 +21,6 @@ import (
 
 func TestValidate(t *testing.T) {
 	t.Parallel()
-	t.Skip("See https://github.com/coder/internal/issues/1602")
 
 	mustTime := func(layout string, value string) time.Time {
 		ti, err := time.Parse(layout, value)
@@ -36,19 +35,38 @@ func TestValidate(t *testing.T) {
 		vmID    string
 	}{{
 		name:    "regular",
-		payload: "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",
-		vmID:    "bd8e7443-24a0-41f3-b949-8baf4fd1c573",
-		date:    mustTime(time.RFC3339, "2023-02-01T00:00:00Z"),
+		payload: "MIIMWwYJKoZIhvcNAQcCoIIMTDCCDEgCAQExDzANBgkqhkiG9w0BAQsFADCCAUUGCSqGSIb3DQEHAaCCATYEggEyeyJsaWNlbnNlVHlwZSI6IiIsIm5vbmNlIjoiMjAyNjA2MjYtMDA1NjQ1IiwicGxhbiI6eyJuYW1lIjoiIiwicHJvZHVjdCI6IiIsInB1Ymxpc2hlciI6IiJ9LCJza3UiOiIyMF8wNC1sdHMtZ2VuMiIsInN1YnNjcmlwdGlvbklkIjoiMDVlOGIyODUtNGNlMS00NmEzLWI0YzktZjUxYmE2N2Q2YWNjIiwidGltZVN0YW1wIjp7ImNyZWF0ZWRPbiI6IjA2LzI1LzI2IDE4OjU2OjQ1IC0wMDAwIiwiZXhwaXJlc09uIjoiMDYvMjYvMjYgMDA6NTY6NDUgLTAwMDAifSwidm1JZCI6ImRjMThkZTU4LTI5MmYtNDc5NC05YTVkLWE0MTkyYmFkMDAzOSJ9oIIJSjCCCUYwggcuoAMCAQICE0EALqSXTgsqkQZ6COsAAAAupJcwDQYJKoZIhvcNAQEMBQAwVzELMAkGA1UEBhMCVVMxHjAcBgNVBAoTFU1pY3Jvc29mdCBDb3Jwb3JhdGlvbjEoMCYGA1UEAxMfTWljcm9zb2Z0IFRMUyBHMiBSU0EgQ0EgT0NTUCAwMjAeFw0yNjA1MTUwNjA1NTdaFw0yNjExMTEwNjA1NTdaMGkxCzAJBgNVBAYTAlVTMQswCQYDVQQIEwJXQTEQMA4GA1UEBxMHUmVkbW9uZDEeMBwGA1UEChMVTWljcm9zb2Z0IENvcnBvcmF0aW9uMRswGQYDVQQDExJtZXRhZGF0YS5henVyZS5jb20wggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQDFUMeP7nY+B8wjCDEynDf1f3RcPLg8xHh2pvyPPItd643gm+mIyCQp46JDPmnjdTQpqwGX2iHhJBgXCMW5eY5s2qJNxUH6sGsl9sSYgOrpiSbnb+ziPqsn+yTsQArkEXeGZY7LAtT37PsTNJHLb5FlULat+ZvGWE9Ul2qjx3Dz06JzzTAJfKharBANq5A1+UaipuAHgNT/pYigWoVOxlbsL101bgu6AUBRV4gkWX6jjSnc2iuGVJww056GuJ4wBlO/rsoJqnpYlYtKnzoOYxoisM46P/mV94ZC05TkkuleiGaq5MhRDtu1yLUSG3nr7nkdJSjuQ+IbppkcMHZT1/7lAgMBAAGjggT3MIIE8zCCAXwGCisGAQQB1nkCBAIEggFsBIIBaAFmAHUA1219ENGn9XfCx+lf1wC/+YLJM1pl4dCzAXMXwMjFaXcAAAGeKkcOowAABAMARjBEAiBQxxq8aaBhsaTybeByYwrTJ8iK115F55DDFQosuQqOVgIgHQ9bewVDO1CJm0A4q6am1+UNcVyTrJYF2HwmORfbyqMAdgDCMX5XRRmjRe5/ON6ykEHrx8IhWiK/f9W1rXaa2Q5SzQAAAZ4qRw6yAAAEAwBHMEUCIQD/bJczftma4J3yW8ykE3Fi/ZnZ+rZFkcjYGxoiB0uPfwIgXv7kbsIcnBZ3vsjPlmFtLJLbI/SLoCf1g1ArGOCkRGQAdQDIo8R/x7OtuTVrAT9qehJt4zpOQ6XGRvmXrTl1mR3PmgAAAZ4qRw7TAAAEAwBGMEQCICAb+0Fr9dMgbLqu43Ub5hX8WIKNXYV3aa9o9OTUhrUFAiBlGy781agUbCEB58We1zK3b2T1IbIhyjx/Baas9IMleDAbBgkrBgEEAYI3FQoEDjAMMAoGCCsGAQUFBwMBMDwGCSsGAQQBgjcVBwQvMC0GJSsGAQQBgjcVCIe91xuB5+tGgoGdLo7QDIfw2h1dg+nDZ4K0o0wCAWQCASAwggELBggrBgEFBQcBAQSB/jCB+zBhBggrBgEFBQcwAoZVaHR0cDovL3d3dy5taWNyb3NvZnQuY29tL3BraW9wcy9jZXJ0cy9NaWNyb3NvZnQlMjBUTFMlMjBHMiUyMFJTQSUyMENBJTIwT0NTUCUyMDAyLmNydDBnBggrBgEFBQcwAoZbaHR0cDovL2NhaXNzdWVycy5taWNyb3NvZnQuY29tL3BraW9wcy9jZXJ0cy9NaWNyb3NvZnQlMjBUTFMlMjBHMiUyMFJTQSUyMENBJTIwT0NTUCUyMDAyLmNydDAtBggrBgEFBQcwAYYhaHR0cDovL29uZW9jc3AubWljcm9zb2Z0LmNvbS9vY3NwMB0GA1UdDgQWBBRoMv9LxNxB8rTiBvbP5VrSH7Z4uzAOBgNVHQ8BAf8EBAMCBaAwOAYDVR0RBDEwL4IZZWFzdHVzLm1ldGFkYXRhLmF6dXJlLmNvbYISbWV0YWRhdGEuYXp1cmUuY29tMAwGA1UdEwEB/wQCMAAwgfEGA1UdHwSB6TCB5jCB46CB4KCB3YZsaHR0cDovL3d3dy5taWNyb3NvZnQuY29tL3BraW9wcy9jcmwvcGFydGl0aW9uL01pY3Jvc29mdCUyMFRMUyUyMEcyJTIwUlNBJTIwQ0ElMjBPQ1NQJTIwMDJfUGFydGl0aW9uMDAwNDUuY3Jshm1odHRwOi8vY3JsMi5taWNyb3NvZnQuY29tL3BraW9wcy9jcmwvcGFydGl0aW9uL01pY3Jvc29mdCUyMFRMUyUyMEcyJTIwUlNBJTIwQ0ElMjBPQ1NQJTIwMDJfUGFydGl0aW9uMDAwNDUuY3JsMGYGA1UdIARfMF0wCAYGZ4EMAQICMFEGDCsGAQQBgjdMg30BATBBMD8GCCsGAQUFBwIBFjNodHRwOi8vd3d3Lm1pY3Jvc29mdC5jb20vcGtpb3BzL0RvY3MvUmVwb3NpdG9yeS5odG0wHwYDVR0jBBgwFoAUuC8zpnxRT38fLdXIFUI4pLIOjy8wEwYDVR0lBAwwCgYIKwYBBQUHAwEwDQYJKoZIhvcNAQEMBQADggIBAJ5k6mdkczx86V+JuUDjTdXRB2hTncJ7sYIVlKgL59VhrchQZKTvqbwyj1SySCQxPkjHZ5uoNC2GxAAFMdE6qLN4mynkp5rHuR87JYptnbysGb7oLcRgDdV84R6ROSOrhgTimjshUmlb5wQBUI857FZ2e0d5gz3oDX+q8FphUCnNRCyDmxd4nwI95OcauuuA4lLW3fxmx7puwSJhpFch2l+ja0ky0C6MhAm/1n+JqNQhr11aHOOhokySw53a7MJLiGBP+/NJZCoW4R353MIzUFSR/1OREEofICVH8JMDd7seYqUhu8QQqGURxn4+04JIC0MCkU+b+R4/qnwyDVZMkKOeWvu5nxb0osTogfiOZ/sJb2sR8cnr7dRrGNENtWXFdVqxedvimxfAGVl0kXPxwIrzAvlFCmzd3CVrsRvuzNqeSzs5h+8D/esqTSSWSgfVYADQE4r9RZNErnxsoRAijIQOwok5zRFwjZ0VwkRUSzFhmQPOoGFLeDNibSE7Gt3yn8ImmFDHzryxwr7RjPjf6lDO/dQrV8yRZkk1zItOspybEctdWplnjp+N6LtBYBLXkNMBwzmGCCwAqP8MN1CAF/sw33jupoke10Jr5cQ9UpiOUEaWhkFE+g3uVTBLSY+zdXtTWBmNQHncgrCOiEgNc3RwmTPvjmeytnQBpkp479S8MYIBmTCCAZUCAQEwbjBXMQswCQYDVQQGEwJVUzEeMBwGA1UEChMVTWljcm9zb2Z0IENvcnBvcmF0aW9uMSgwJgYDVQQDEx9NaWNyb3NvZnQgVExTIEcyIFJTQSBDQSBPQ1NQIDAyAhNBAC6kl04LKpEGegjrAAAALqSXMA0GCSqGSIb3DQEBCwUAMA0GCSqGSIb3DQEBAQUABIIBAB7JzdET7tluzF+I9yyaCgmsWlPmvndXZAWtq6YCJqEYvy4OBf4smb/H7e5rK72yaO1jMZnZ6/0IYl1N4DxeNSX3LuLirU7w2r0+sNypte+JH+Gzf1vBO9y57ARCHLLXPRS33T1XQVTsCXPu+7BeH5m6xNIcShxqAlWAAD2g4iR8uqhwJ6FLiA0LHTevqfxC0MQfEmTQE33eifwT3OYgujrLXqalM7MyQncZDIXXJWdgYtyMRh22QGDRb4FAXYs/BPvOBwzlUQuV3TWaHtAwdQUP1jgxlkXxa/xp0lz7O/OnihXY4H8F/vGfFtr3h26inmfsI7nyKiyfopaE6aD6/9c=",
+		vmID:    "dc18de58-292f-4794-9a5d-a4192bad0039",
+		// This cert uses intermediates:
+		//  1. Microsoft TLS G2 RSA CA OCSP 02 (expires 2029-06-03T20:03:00Z)
+		//  2. Microsoft TLS RSA Root G2       (expires 2029-06-19T23:59:59Z)
+		// It uses root:
+		//  DigiCert Global Root G2            (expires 2038-01-15T12:00:00Z)
+		// So this test should be good until 2038 provided that we don't remove the above intermediates, and the
+		// root doesn't get removed from OS trust stores (would be very surprising and a huge security deal).
+		date: mustTime(time.RFC3339, "2026-06-25T00:00:00Z"),
 	}, {
 		name:    "govcloud",
 		payload: "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",
 		vmID:    "990878d4-068a-4ac4-9ee9-1231d2218ef2",
-		date:    mustTime(time.RFC3339, "2023-04-01T00:00:00Z"),
+		// This cert uses intermediate:
+		//  Microsoft Azure TLS Issuing CA 05  (expires 2024-06-27T23:59:59Z)
+		// It uses root:
+		//  DigiCert Global Root G2            (expires 2038-01-15T12:00:00Z)
+		// So this test should be good until 2038 provided that we don't remove the above intermediates, and the
+		// root doesn't get removed from OS trust stores (would be very surprising and a huge security deal).
+		date: mustTime(time.RFC3339, "2023-04-01T00:00:00Z"),
 	}, {
 		name:    "rsa",
 		payload: "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",
 		vmID:    "960a4b4a-dab2-44ef-9b73-7753043b4f16",
-		date:    mustTime(time.RFC3339, "2024-04-22T17:32:44Z"),
+		// This cert uses intermediate:
+		//  Microsoft Azure RSA TLS Issuing CA 08  (expires 2026-08-25T23:59:59Z)
+		// It uses root:
+		//  DigiCert Global Root G2                (expires 2038-01-15T12:00:00Z)
+		// So this test should be good until 2038 provided that we don't remove the above intermediates, and the
+		// root doesn't get removed from OS trust stores (would be very surprising and a huge security deal).
+		date: mustTime(time.RFC3339, "2024-04-22T17:32:44Z"),
 	}} {
 		t.Run(tc.name, func(t *testing.T) {
 			t.Parallel()
@@ -62,31 +80,6 @@ func TestValidate(t *testing.T) {
 	}
 }
 
-func TestExpiresSoon(t *testing.T) {
-	t.Parallel()
-	// TODO (@kylecarbs): It's unknown why Microsoft does not have new certificates live...
-	// The certificate is automatically fetched if it's not found in our database,
-	// so in a worst-case scenario expired certificates will only impact 100% airgapped users.
-	t.Skip()
-	const threshold = 1
-
-	certs, err := azureidentity.ParseCertificates()
-	require.NoError(t, err)
-
-	for _, cert := range certs {
-		expiresSoon := cert.NotAfter.Before(time.Now().AddDate(0, threshold, 0))
-		if expiresSoon {
-			t.Errorf("certificate expires within %d months %s: %s", threshold, cert.NotAfter, cert.Subject.CommonName)
-		} else {
-			url := "no issuing url"
-			if len(cert.IssuingCertificateURL) > 0 {
-				url = cert.IssuingCertificateURL[0]
-			}
-			t.Logf("certificate %q doesn't expire for a while (%s)", cert.Subject.CommonName, url)
-		}
-	}
-}
-
 func TestIsAllowedCertificateURL(t *testing.T) {
 	t.Parallel()
 	tests := []struct {