diff --git a/connector/oidc/oidc.go b/connector/oidc/oidc.go
index 728bdf6a..0310266c 100644
--- a/connector/oidc/oidc.go
+++ b/connector/oidc/oidc.go
@@ -6,6 +6,9 @@ import (
 	"errors"
 	"fmt"
 	"net/http"
+	"net/url"
+	"strings"
+	"sync"
 
 	"github.com/Sirupsen/logrus"
 	"github.com/coreos/go-oidc"
@@ -21,7 +24,50 @@ type Config struct {
 	ClientSecret string `json:"clientSecret"`
 	RedirectURI  string `json:"redirectURI"`
 
+	// Causes client_secret to be passed as POST parameters instead of basic
+	// auth. This is specifically "NOT RECOMMENDED" by the OAuth2 RFC, but some
+	// providers require it.
+	//
+	// https://tools.ietf.org/html/rfc6749#section-2.3.1
+	BasicAuthUnsupported *bool `json:"basicAuthUnsupported"`
+
 	Scopes []string `json:"scopes"` // defaults to "profile" and "email"
+
+}
+
+// Domains that don't support basic auth. golang.org/x/oauth2 has an internal
+// list, but it only matches specific URLs, not top level domains.
+var brokenAuthHeaderDomains = []string{
+	// See: https://github.com/coreos/dex/issues/859
+	"okta.com",
+	"oktapreview.com",
+}
+
+// Detect auth header provider issues for known providers. This lets users
+// avoid having to explicitly set "basicAuthUnsupported" in their config.
+//
+// Setting the config field always overrides values returned by this function.
+func knownBrokenAuthHeaderProvider(issuerURL string) bool {
+	if u, err := url.Parse(issuerURL); err == nil {
+		for _, host := range brokenAuthHeaderDomains {
+			if u.Host == host || strings.HasSuffix(u.Host, "."+host) {
+				return true
+			}
+		}
+	}
+	return false
+}
+
+// golang.org/x/oauth2 doesn't do internal locking. Need to do it in this
+// package ourselves and hope that other packages aren't calling it at the
+// same time.
+var registerMu = new(sync.Mutex)
+
+func registerBrokenAuthHeaderProvider(url string) {
+	registerMu.Lock()
+	defer registerMu.Unlock()
+
+	oauth2.RegisterBrokenAuthHeaderProvider(url)
 }
 
 // Open returns a connector which can be used to login users through an upstream
@@ -35,6 +81,15 @@ func (c *Config) Open(logger logrus.FieldLogger) (conn connector.Connector, err
 		return nil, fmt.Errorf("failed to get provider: %v", err)
 	}
 
+	if c.BasicAuthUnsupported != nil {
+		// Setting "basicAuthUnsupported" always overrides our detection.
+		if *c.BasicAuthUnsupported {
+			registerBrokenAuthHeaderProvider(provider.Endpoint().TokenURL)
+		}
+	} else if knownBrokenAuthHeaderProvider(c.Issuer) {
+		registerBrokenAuthHeaderProvider(provider.Endpoint().TokenURL)
+	}
+
 	scopes := []string{oidc.ScopeOpenID}
 	if len(c.Scopes) > 0 {
 		scopes = append(scopes, c.Scopes...)
diff --git a/connector/oidc/oidc_test.go b/connector/oidc/oidc_test.go
new file mode 100644
index 00000000..b3f609d1
--- /dev/null
+++ b/connector/oidc/oidc_test.go
@@ -0,0 +1,23 @@
+package oidc
+
+import "testing"
+
+func TestKnownBrokenAuthHeaderProvider(t *testing.T) {
+	tests := []struct {
+		issuerURL string
+		expect    bool
+	}{
+		{"https://dev.oktapreview.com", true},
+		{"https://dev.okta.com", true},
+		{"https://okta.com", true},
+		{"https://dev.oktaaccounts.com", false},
+		{"https://accounts.google.com", false},
+	}
+
+	for _, tc := range tests {
+		got := knownBrokenAuthHeaderProvider(tc.issuerURL)
+		if got != tc.expect {
+			t.Errorf("knownBrokenAuthHeaderProvider(%q), want=%t, got=%t", tc.issuerURL, tc.expect, got)
+		}
+	}
+}