Merge pull request #221 from mattmoyer/use-https-dex

Add support for custom CA bundle in CLI and UpstreamOIDCProvider.

.golangci.yaml

@@ -60,7 +60,7 @@ issues:
 
 linters-settings:
   funlen:
-    lines: 125
+    lines: 150
     statements: 50
   goheader:
     template: |-

apis/supervisor/idp/v1alpha1/types_tls.go.tmpl

@@ -0,0 +1,11 @@
+// Copyright 2020 the Pinniped contributors. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package v1alpha1
+
+// Configuration for TLS parameters related to identity provider integration.
+type TLSSpec struct {
+	// X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+	// +optional
+	CertificateAuthorityData string `json:"certificateAuthorityData,omitempty"`
+}

apis/supervisor/idp/v1alpha1/types_upstreamoidcprovider.go.tmpl

@@ -75,6 +75,10 @@ type UpstreamOIDCProviderSpec struct {
 	// +kubebuilder:validation:Pattern=`^https://`
 	Issuer string `json:"issuer"`
 
+	// TLS configuration for discovery/JWKS requests to the issuer.
+	// +optional
+	TLS *TLSSpec `json:"tls,omitempty"`
+
 	// AuthorizationConfig holds information about how to form the OAuth2 authorization request
 	// parameters to be used with this OIDC identity provider.
 	// +optional

cmd/pinniped/cmd/login_oidc.go

@@ -4,7 +4,12 @@
 package cmd
 
 import (
+	"crypto/tls"
+	"crypto/x509"
 	"encoding/json"
+	"fmt"
+	"io/ioutil"
+	"net/http"
 	"os"
 	"path/filepath"
 
@@ -36,6 +41,7 @@ func oidcLoginCommand(loginFunc func(issuer string, clientID string, opts ...oid
 		scopes            []string
 		skipBrowser       bool
 		sessionCachePath  string
+		caBundlePaths     []string
 		debugSessionCache bool
 	)
 	cmd.Flags().StringVar(&issuer, "issuer", "", "OpenID Connect issuer URL.")
@@ -44,6 +50,7 @@ func oidcLoginCommand(loginFunc func(issuer string, clientID string, opts ...oid
 	cmd.Flags().StringSliceVar(&scopes, "scopes", []string{"offline_access", "openid", "email", "profile"}, "OIDC scopes to request during login.")
 	cmd.Flags().BoolVar(&skipBrowser, "skip-browser", false, "Skip opening the browser (just print the URL).")
 	cmd.Flags().StringVar(&sessionCachePath, "session-cache", filepath.Join(mustGetConfigDir(), "sessions.yaml"), "Path to session cache file.")
+	cmd.Flags().StringSliceVar(&caBundlePaths, "ca-bundle", nil, "Path to TLS certificate authority bundle (PEM format, optional, can be repeated).")
 	cmd.Flags().BoolVar(&debugSessionCache, "debug-session-cache", false, "Print debug logs related to the session cache.")
 	mustMarkHidden(&cmd, "debug-session-cache")
 	mustMarkRequired(&cmd, "issuer", "client-id")
@@ -80,6 +87,27 @@ func oidcLoginCommand(loginFunc func(issuer string, clientID string, opts ...oid
 			}))
 		}
 
+		if len(caBundlePaths) > 0 {
+			pool := x509.NewCertPool()
+			for _, p := range caBundlePaths {
+				pem, err := ioutil.ReadFile(p)
+				if err != nil {
+					return fmt.Errorf("could not read --ca-bundle: %w", err)
+				}
+				pool.AppendCertsFromPEM(pem)
+			}
+			tlsConfig := tls.Config{
+				RootCAs:    pool,
+				MinVersion: tls.VersionTLS12,
+			}
+			opts = append(opts, oidcclient.WithClient(&http.Client{
+				Transport: &http.Transport{
+					Proxy:           http.ProxyFromEnvironment,
+					TLSClientConfig: &tlsConfig,
+				},
+			}))
+		}
+
 		tok, err := loginFunc(issuer, clientID, opts...)
 		if err != nil {
 			return err

cmd/pinniped/cmd/login_oidc_test.go

@@ -40,6 +40,7 @@ func TestLoginOIDCCommand(t *testing.T) {
 				  oidc --issuer ISSUER --client-id CLIENT_ID [flags]
 
 				Flags:
+					  --ca-bundle strings      Path to TLS certificate authority bundle (PEM format, optional, can be repeated).
 					  --client-id string       OpenID Connect client ID.
 				  -h, --help                   help for oidc
 					  --issuer string          OpenID Connect issuer URL.

deploy/supervisor/idp.supervisor.pinniped.dev_upstreamoidcproviders.yaml

@@ -98,6 +98,15 @@ spec:
                 minLength: 1
                 pattern: ^https://
                 type: string
+              tls:
+                description: TLS configuration for discovery/JWKS requests to the
+                  issuer.
+                properties:
+                  certificateAuthorityData:
+                    description: X.509 Certificate Authority (base64-encoded PEM bundle).
+                      If omitted, a default set of system roots will be trusted.
+                    type: string
+                type: object
             required:
             - client
             - issuer

generated/1.17/README.adoc

@@ -373,6 +373,23 @@ OIDCClient contains information about an OIDC client (e.g., client ID and client
 |===
 
 
+[id="{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-tlsspec"]
+==== TLSSpec 
+
+Configuration for TLS parameters related to identity provider integration.
+
+.Appears In:
+****
+- xref:{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-upstreamoidcproviderspec[$$UpstreamOIDCProviderSpec$$]
+****
+
+[cols="25a,75a", options="header"]
+|===
+| Field | Description
+| *`certificateAuthorityData`* __string__ | X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+|===
+
+
 [id="{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-upstreamoidcprovider"]
 ==== UpstreamOIDCProvider 
 
@@ -409,6 +426,7 @@ Spec for configuring an OIDC identity provider.
 |===
 | Field | Description
 | *`issuer`* __string__ | Issuer is the issuer URL of this OIDC identity provider, i.e., where to fetch /.well-known/openid-configuration.
+| *`tls`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-tlsspec[$$TLSSpec$$]__ | TLS configuration for discovery/JWKS requests to the issuer.
 | *`authorizationConfig`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-oidcauthorizationconfig[$$OIDCAuthorizationConfig$$]__ | AuthorizationConfig holds information about how to form the OAuth2 authorization request parameters to be used with this OIDC identity provider.
 | *`claims`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-oidcclaims[$$OIDCClaims$$]__ | Claims provides the names of token claims that will be used when inspecting an identity from this OIDC identity provider.
 | *`client`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-17-apis-supervisor-idp-v1alpha1-oidcclient[$$OIDCClient$$]__ | OIDCClient contains OIDC client information to be used used with this OIDC identity provider.

generated/1.17/apis/supervisor/idp/v1alpha1/types_tls.go

@@ -0,0 +1,11 @@
+// Copyright 2020 the Pinniped contributors. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package v1alpha1
+
+// Configuration for TLS parameters related to identity provider integration.
+type TLSSpec struct {
+	// X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+	// +optional
+	CertificateAuthorityData string `json:"certificateAuthorityData,omitempty"`
+}

generated/1.17/apis/supervisor/idp/v1alpha1/types_upstreamoidcprovider.go

@@ -75,6 +75,10 @@ type UpstreamOIDCProviderSpec struct {
 	// +kubebuilder:validation:Pattern=`^https://`
 	Issuer string `json:"issuer"`
 
+	// TLS configuration for discovery/JWKS requests to the issuer.
+	// +optional
+	TLS *TLSSpec `json:"tls,omitempty"`
+
 	// AuthorizationConfig holds information about how to form the OAuth2 authorization request
 	// parameters to be used with this OIDC identity provider.
 	// +optional

generated/1.17/apis/supervisor/idp/v1alpha1/zz_generated.deepcopy.go

@@ -81,6 +81,22 @@ func (in *OIDCClient) DeepCopy() *OIDCClient {
 	return out
 }
 
+// DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
+func (in *TLSSpec) DeepCopyInto(out *TLSSpec) {
+	*out = *in
+	return
+}
+
+// DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new TLSSpec.
+func (in *TLSSpec) DeepCopy() *TLSSpec {
+	if in == nil {
+		return nil
+	}
+	out := new(TLSSpec)
+	in.DeepCopyInto(out)
+	return out
+}
+
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *UpstreamOIDCProvider) DeepCopyInto(out *UpstreamOIDCProvider) {
 	*out = *in
@@ -145,6 +161,11 @@ func (in *UpstreamOIDCProviderList) DeepCopyObject() runtime.Object {
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *UpstreamOIDCProviderSpec) DeepCopyInto(out *UpstreamOIDCProviderSpec) {
 	*out = *in
+	if in.TLS != nil {
+		in, out := &in.TLS, &out.TLS
+		*out = new(TLSSpec)
+		**out = **in
+	}
 	in.AuthorizationConfig.DeepCopyInto(&out.AuthorizationConfig)
 	out.Claims = in.Claims
 	out.Client = in.Client

generated/1.17/crds/idp.supervisor.pinniped.dev_upstreamoidcproviders.yaml

@@ -98,6 +98,15 @@ spec:
                 minLength: 1
                 pattern: ^https://
                 type: string
+              tls:
+                description: TLS configuration for discovery/JWKS requests to the
+                  issuer.
+                properties:
+                  certificateAuthorityData:
+                    description: X.509 Certificate Authority (base64-encoded PEM bundle).
+                      If omitted, a default set of system roots will be trusted.
+                    type: string
+                type: object
             required:
             - client
             - issuer

generated/1.18/README.adoc

@@ -373,6 +373,23 @@ OIDCClient contains information about an OIDC client (e.g., client ID and client
 |===
 
 
+[id="{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-tlsspec"]
+==== TLSSpec 
+
+Configuration for TLS parameters related to identity provider integration.
+
+.Appears In:
+****
+- xref:{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-upstreamoidcproviderspec[$$UpstreamOIDCProviderSpec$$]
+****
+
+[cols="25a,75a", options="header"]
+|===
+| Field | Description
+| *`certificateAuthorityData`* __string__ | X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+|===
+
+
 [id="{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-upstreamoidcprovider"]
 ==== UpstreamOIDCProvider 
 
@@ -409,6 +426,7 @@ Spec for configuring an OIDC identity provider.
 |===
 | Field | Description
 | *`issuer`* __string__ | Issuer is the issuer URL of this OIDC identity provider, i.e., where to fetch /.well-known/openid-configuration.
+| *`tls`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-tlsspec[$$TLSSpec$$]__ | TLS configuration for discovery/JWKS requests to the issuer.
 | *`authorizationConfig`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-oidcauthorizationconfig[$$OIDCAuthorizationConfig$$]__ | AuthorizationConfig holds information about how to form the OAuth2 authorization request parameters to be used with this OIDC identity provider.
 | *`claims`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-oidcclaims[$$OIDCClaims$$]__ | Claims provides the names of token claims that will be used when inspecting an identity from this OIDC identity provider.
 | *`client`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-18-apis-supervisor-idp-v1alpha1-oidcclient[$$OIDCClient$$]__ | OIDCClient contains OIDC client information to be used used with this OIDC identity provider.

generated/1.18/apis/supervisor/idp/v1alpha1/types_tls.go

@@ -0,0 +1,11 @@
+// Copyright 2020 the Pinniped contributors. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package v1alpha1
+
+// Configuration for TLS parameters related to identity provider integration.
+type TLSSpec struct {
+	// X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+	// +optional
+	CertificateAuthorityData string `json:"certificateAuthorityData,omitempty"`
+}

generated/1.18/apis/supervisor/idp/v1alpha1/types_upstreamoidcprovider.go

@@ -75,6 +75,10 @@ type UpstreamOIDCProviderSpec struct {
 	// +kubebuilder:validation:Pattern=`^https://`
 	Issuer string `json:"issuer"`
 
+	// TLS configuration for discovery/JWKS requests to the issuer.
+	// +optional
+	TLS *TLSSpec `json:"tls,omitempty"`
+
 	// AuthorizationConfig holds information about how to form the OAuth2 authorization request
 	// parameters to be used with this OIDC identity provider.
 	// +optional

generated/1.18/apis/supervisor/idp/v1alpha1/zz_generated.deepcopy.go

@@ -81,6 +81,22 @@ func (in *OIDCClient) DeepCopy() *OIDCClient {
 	return out
 }
 
+// DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
+func (in *TLSSpec) DeepCopyInto(out *TLSSpec) {
+	*out = *in
+	return
+}
+
+// DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new TLSSpec.
+func (in *TLSSpec) DeepCopy() *TLSSpec {
+	if in == nil {
+		return nil
+	}
+	out := new(TLSSpec)
+	in.DeepCopyInto(out)
+	return out
+}
+
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *UpstreamOIDCProvider) DeepCopyInto(out *UpstreamOIDCProvider) {
 	*out = *in
@@ -145,6 +161,11 @@ func (in *UpstreamOIDCProviderList) DeepCopyObject() runtime.Object {
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *UpstreamOIDCProviderSpec) DeepCopyInto(out *UpstreamOIDCProviderSpec) {
 	*out = *in
+	if in.TLS != nil {
+		in, out := &in.TLS, &out.TLS
+		*out = new(TLSSpec)
+		**out = **in
+	}
 	in.AuthorizationConfig.DeepCopyInto(&out.AuthorizationConfig)
 	out.Claims = in.Claims
 	out.Client = in.Client

generated/1.18/crds/idp.supervisor.pinniped.dev_upstreamoidcproviders.yaml

@@ -98,6 +98,15 @@ spec:
                 minLength: 1
                 pattern: ^https://
                 type: string
+              tls:
+                description: TLS configuration for discovery/JWKS requests to the
+                  issuer.
+                properties:
+                  certificateAuthorityData:
+                    description: X.509 Certificate Authority (base64-encoded PEM bundle).
+                      If omitted, a default set of system roots will be trusted.
+                    type: string
+                type: object
             required:
             - client
             - issuer

generated/1.19/README.adoc

@@ -373,6 +373,23 @@ OIDCClient contains information about an OIDC client (e.g., client ID and client
 |===
 
 
+[id="{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-tlsspec"]
+==== TLSSpec 
+
+Configuration for TLS parameters related to identity provider integration.
+
+.Appears In:
+****
+- xref:{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-upstreamoidcproviderspec[$$UpstreamOIDCProviderSpec$$]
+****
+
+[cols="25a,75a", options="header"]
+|===
+| Field | Description
+| *`certificateAuthorityData`* __string__ | X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+|===
+
+
 [id="{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-upstreamoidcprovider"]
 ==== UpstreamOIDCProvider 
 
@@ -409,6 +426,7 @@ Spec for configuring an OIDC identity provider.
 |===
 | Field | Description
 | *`issuer`* __string__ | Issuer is the issuer URL of this OIDC identity provider, i.e., where to fetch /.well-known/openid-configuration.
+| *`tls`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-tlsspec[$$TLSSpec$$]__ | TLS configuration for discovery/JWKS requests to the issuer.
 | *`authorizationConfig`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-oidcauthorizationconfig[$$OIDCAuthorizationConfig$$]__ | AuthorizationConfig holds information about how to form the OAuth2 authorization request parameters to be used with this OIDC identity provider.
 | *`claims`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-oidcclaims[$$OIDCClaims$$]__ | Claims provides the names of token claims that will be used when inspecting an identity from this OIDC identity provider.
 | *`client`* __xref:{anchor_prefix}-go-pinniped-dev-generated-1-19-apis-supervisor-idp-v1alpha1-oidcclient[$$OIDCClient$$]__ | OIDCClient contains OIDC client information to be used used with this OIDC identity provider.

generated/1.19/apis/supervisor/idp/v1alpha1/types_tls.go

@@ -0,0 +1,11 @@
+// Copyright 2020 the Pinniped contributors. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package v1alpha1
+
+// Configuration for TLS parameters related to identity provider integration.
+type TLSSpec struct {
+	// X.509 Certificate Authority (base64-encoded PEM bundle). If omitted, a default set of system roots will be trusted.
+	// +optional
+	CertificateAuthorityData string `json:"certificateAuthorityData,omitempty"`
+}

generated/1.19/apis/supervisor/idp/v1alpha1/types_upstreamoidcprovider.go

@@ -75,6 +75,10 @@ type UpstreamOIDCProviderSpec struct {
 	// +kubebuilder:validation:Pattern=`^https://`
 	Issuer string `json:"issuer"`
 
+	// TLS configuration for discovery/JWKS requests to the issuer.
+	// +optional
+	TLS *TLSSpec `json:"tls,omitempty"`
+
 	// AuthorizationConfig holds information about how to form the OAuth2 authorization request
 	// parameters to be used with this OIDC identity provider.
 	// +optional

generated/1.19/apis/supervisor/idp/v1alpha1/zz_generated.deepcopy.go

@@ -81,6 +81,22 @@ func (in *OIDCClient) DeepCopy() *OIDCClient {
 	return out
 }
 
+// DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
+func (in *TLSSpec) DeepCopyInto(out *TLSSpec) {
+	*out = *in
+	return
+}
+
+// DeepCopy is an autogenerated deepcopy function, copying the receiver, creating a new TLSSpec.
+func (in *TLSSpec) DeepCopy() *TLSSpec {
+	if in == nil {
+		return nil
+	}
+	out := new(TLSSpec)
+	in.DeepCopyInto(out)
+	return out
+}
+
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *UpstreamOIDCProvider) DeepCopyInto(out *UpstreamOIDCProvider) {
 	*out = *in
@@ -145,6 +161,11 @@ func (in *UpstreamOIDCProviderList) DeepCopyObject() runtime.Object {
 // DeepCopyInto is an autogenerated deepcopy function, copying the receiver, writing into out. in must be non-nil.
 func (in *UpstreamOIDCProviderSpec) DeepCopyInto(out *UpstreamOIDCProviderSpec) {
 	*out = *in
+	if in.TLS != nil {
+		in, out := &in.TLS, &out.TLS
+		*out = new(TLSSpec)
+		**out = **in
+	}
 	in.AuthorizationConfig.DeepCopyInto(&out.AuthorizationConfig)
 	out.Claims = in.Claims
 	out.Client = in.Client

generated/1.19/crds/idp.supervisor.pinniped.dev_upstreamoidcproviders.yaml

@@ -98,6 +98,15 @@ spec:
                 minLength: 1
                 pattern: ^https://
                 type: string
+              tls:
+                description: TLS configuration for discovery/JWKS requests to the
+                  issuer.
+                properties:
+                  certificateAuthorityData:
+                    description: X.509 Certificate Authority (base64-encoded PEM bundle).
+                      If omitted, a default set of system roots will be trusted.
+                    type: string
+                type: object
             required:
             - client
             - issuer

hack/prepare-for-integration-tests.sh

@@ -265,6 +265,11 @@ if ! tilt_mode; then
   popd >/dev/null
 fi
 
+#
+# Download the test CA bundle that was generated in the Dex pod.
+#
+test_ca_bundle_pem="$(kubectl exec -n dex deployment/dex -- cat /var/certs/ca.pem)"
+
 #
 # Create the environment file
 #
@@ -287,7 +292,8 @@ export PINNIPED_TEST_SUPERVISOR_CUSTOM_LABELS='${supervisor_custom_labels}'
 export PINNIPED_TEST_SUPERVISOR_HTTP_ADDRESS="127.0.0.1:12345"
 export PINNIPED_TEST_SUPERVISOR_HTTPS_ADDRESS="localhost:12344"
 export PINNIPED_TEST_PROXY=http://127.0.0.1:12346
-export PINNIPED_TEST_CLI_OIDC_ISSUER=http://dex.dex.svc.cluster.local/dex
+export PINNIPED_TEST_CLI_OIDC_ISSUER=https://dex.dex.svc.cluster.local/dex
+export PINNIPED_TEST_CLI_OIDC_ISSUER_CA_BUNDLE="${test_ca_bundle_pem}"
 export PINNIPED_TEST_CLI_OIDC_CLIENT_ID=pinniped-cli
 export PINNIPED_TEST_CLI_OIDC_LOCALHOST_PORT=48095
 export PINNIPED_TEST_CLI_OIDC_USERNAME=pinny@example.com

internal/controller/supervisorconfig/upstreamwatcher/upstreamwatcher.go

@@ -6,7 +6,11 @@ package upstreamwatcher
 
 import (
 	"context"
+	"crypto/tls"
+	"crypto/x509"
+	"encoding/base64"
 	"fmt"
+	"net/http"
 	"net/url"
 	"sort"
 	"time"
@@ -48,10 +52,12 @@ const (
 	reasonMissingKeys          = "SecretMissingKeys"
 	reasonSuccess              = "Success"
 	reasonUnreachable          = "Unreachable"
+	reasonInvalidTLSConfig     = "InvalidTLSConfig"
 	reasonInvalidResponse      = "InvalidResponse"
 
 	// Errors that are generated by our reconcile process.
-	errFailureStatus = constable.Error("UpstreamOIDCProvider has a failing condition")
+	errFailureStatus  = constable.Error("UpstreamOIDCProvider has a failing condition")
+	errNoCertificates = constable.Error("no certificates found")
 )
 
 // IDPCache is a thread safe cache that holds a list of validated upstream OIDC IDP configurations.
@@ -59,13 +65,39 @@ type IDPCache interface {
 	SetIDPList([]provider.UpstreamOIDCIdentityProvider)
 }
 
+// lruValidatorCache caches the *oidc.Provider associated with a particular issuer/TLS configuration.
+type lruValidatorCache struct{ cache *cache.Expiring }
+
+func (c *lruValidatorCache) getProvider(spec *v1alpha1.UpstreamOIDCProviderSpec) *oidc.Provider {
+	if result, ok := c.cache.Get(c.cacheKey(spec)); ok {
+		return result.(*oidc.Provider)
+	}
+	return nil
+}
+
+func (c *lruValidatorCache) putProvider(spec *v1alpha1.UpstreamOIDCProviderSpec, provider *oidc.Provider) {
+	c.cache.Set(c.cacheKey(spec), provider, validatorCacheTTL)
+}
+
+func (c *lruValidatorCache) cacheKey(spec *v1alpha1.UpstreamOIDCProviderSpec) interface{} {
+	var key struct{ issuer, caBundle string }
+	key.issuer = spec.Issuer
+	if spec.TLS != nil {
+		key.caBundle = spec.TLS.CertificateAuthorityData
+	}
+	return key
+}
+
 type controller struct {
 	cache          IDPCache
 	log            logr.Logger
 	client         pinnipedclientset.Interface
 	providers      idpinformers.UpstreamOIDCProviderInformer
 	secrets        corev1informers.SecretInformer
-	validatorCache *cache.Expiring
+	validatorCache interface {
+		getProvider(spec *v1alpha1.UpstreamOIDCProviderSpec) *oidc.Provider
+		putProvider(spec *v1alpha1.UpstreamOIDCProviderSpec, provider *oidc.Provider)
+	}
 }
 
 // New instantiates a new controllerlib.Controller which will populate the provided IDPCache.
@@ -82,7 +114,7 @@ func New(
 		client:         client,
 		providers:      providers,
 		secrets:        secrets,
-		validatorCache: cache.NewExpiring(),
+		validatorCache: &lruValidatorCache{cache: cache.NewExpiring()},
 	}
 	filter := pinnipedcontroller.MatchAnythingFilter(pinnipedcontroller.SingletonQueue())
 	return controllerlib.New(
@@ -197,15 +229,22 @@ func (c *controller) validateSecret(upstream *v1alpha1.UpstreamOIDCProvider, res
 // validateIssuer validates the .spec.issuer field, performs OIDC discovery, and returns the appropriate OIDCDiscoverySucceeded condition.
 func (c *controller) validateIssuer(ctx context.Context, upstream *v1alpha1.UpstreamOIDCProvider, result *provider.UpstreamOIDCIdentityProvider) *v1alpha1.Condition {
 	// Get the provider (from cache if possible).
-	var discoveredProvider *oidc.Provider
+	discoveredProvider := c.validatorCache.getProvider(&upstream.Spec)
-	if cached, ok := c.validatorCache.Get(upstream.Spec.Issuer); ok {
-		discoveredProvider = cached.(*oidc.Provider)
-	}
 
 	// If the provider does not exist in the cache, do a fresh discovery lookup and save to the cache.
 	if discoveredProvider == nil {
-		var err error
+		tlsConfig, err := getTLSConfig(upstream)
-		discoveredProvider, err = oidc.NewProvider(ctx, upstream.Spec.Issuer)
+		if err != nil {
+			return &v1alpha1.Condition{
+				Type:    typeOIDCDiscoverySucceeded,
+				Status:  v1alpha1.ConditionFalse,
+				Reason:  reasonInvalidTLSConfig,
+				Message: err.Error(),
+			}
+		}
+		httpClient := &http.Client{Transport: &http.Transport{TLSClientConfig: tlsConfig}}
+
+		discoveredProvider, err = oidc.NewProvider(oidc.ClientContext(ctx, httpClient), upstream.Spec.Issuer)
 		if err != nil {
 			return &v1alpha1.Condition{
 				Type:    typeOIDCDiscoverySucceeded,
@@ -216,7 +255,7 @@ func (c *controller) validateIssuer(ctx context.Context, upstream *v1alpha1.Upst
 		}
 
 		// Update the cache with the newly discovered value.
-		c.validatorCache.Set(upstream.Spec.Issuer, discoveredProvider, validatorCacheTTL)
+		c.validatorCache.putProvider(&upstream.Spec, discoveredProvider)
 	}
 
 	// Parse out and validate the discovered authorize endpoint.
@@ -248,6 +287,28 @@ func (c *controller) validateIssuer(ctx context.Context, upstream *v1alpha1.Upst
 	}
 }
 
+func getTLSConfig(upstream *v1alpha1.UpstreamOIDCProvider) (*tls.Config, error) {
+	result := tls.Config{
+		MinVersion: tls.VersionTLS12,
+	}
+
+	if upstream.Spec.TLS == nil || upstream.Spec.TLS.CertificateAuthorityData == "" {
+		return &result, nil
+	}
+
+	bundle, err := base64.StdEncoding.DecodeString(upstream.Spec.TLS.CertificateAuthorityData)
+	if err != nil {
+		return nil, fmt.Errorf("spec.certificateAuthorityData is invalid: %w", err)
+	}
+
+	result.RootCAs = x509.NewCertPool()
+	if !result.RootCAs.AppendCertsFromPEM(bundle) {
+		return nil, fmt.Errorf("spec.certificateAuthorityData is invalid: %w", errNoCertificates)
+	}
+
+	return &result, nil
+}
+
 func (c *controller) updateStatus(ctx context.Context, upstream *v1alpha1.UpstreamOIDCProvider, conditions []*v1alpha1.Condition) {
 	log := c.log.WithValues("namespace", upstream.Namespace, "name", upstream.Name)
 	updated := upstream.DeepCopy()

internal/controller/supervisorconfig/upstreamwatcher/upstreamwatcher_test.go

@@ -5,9 +5,9 @@ package upstreamwatcher
 
 import (
 	"context"
+	"encoding/base64"
 	"encoding/json"
 	"net/http"
-	"net/http/httptest"
 	"net/url"
 	"strings"
 	"testing"
@@ -25,6 +25,7 @@ import (
 	pinnipedinformers "go.pinniped.dev/generated/1.19/client/supervisor/informers/externalversions"
 	"go.pinniped.dev/internal/controllerlib"
 	"go.pinniped.dev/internal/oidc/provider"
+	"go.pinniped.dev/internal/testutil"
 	"go.pinniped.dev/internal/testutil/testlogger"
 )
 
@@ -34,7 +35,8 @@ func TestController(t *testing.T) {
 	earlier := metav1.NewTime(now.Add(-1 * time.Hour).UTC())
 
 	// Start another test server that answers discovery successfully.
-	testIssuer := newTestIssuer(t)
+	testIssuerCA, testIssuerURL := newTestIssuer(t)
+	testIssuerCABase64 := base64.StdEncoding.EncodeToString([]byte(testIssuerCA))
 	testIssuerAuthorizeURL, err := url.Parse("https://example.com/authorize")
 	require.NoError(t, err)
 
@@ -65,7 +67,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL,
+					Issuer:              testIssuerURL,
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: testAdditionalScopes},
 				},
@@ -106,7 +109,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL,
+					Issuer:              testIssuerURL,
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: testAdditionalScopes},
 				},
@@ -151,7 +155,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL,
+					Issuer:              testIssuerURL,
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: testAdditionalScopes},
 				},
@@ -190,6 +195,102 @@ func TestController(t *testing.T) {
 				},
 			}},
 		},
+		{
+			name: "TLS CA bundle is invalid base64",
+			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
+				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: "test-name"},
+				Spec: v1alpha1.UpstreamOIDCProviderSpec{
+					Issuer: testIssuerURL,
+					TLS: &v1alpha1.TLSSpec{
+						CertificateAuthorityData: "invalid-base64",
+					},
+					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
+					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: append(testAdditionalScopes, "xyz", "openid")},
+				},
+			}},
+			inputSecrets: []runtime.Object{&corev1.Secret{
+				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testSecretName},
+				Type:       "secrets.pinniped.dev/oidc-client",
+				Data:       testValidSecretData,
+			}},
+			wantErr: controllerlib.ErrSyntheticRequeue.Error(),
+			wantLogs: []string{
+				`upstream-observer "level"=0 "msg"="updated condition" "name"="test-name" "namespace"="test-namespace" "message"="loaded client credentials" "reason"="Success" "status"="True" "type"="ClientCredentialsValid"`,
+				`upstream-observer "level"=0 "msg"="updated condition" "name"="test-name" "namespace"="test-namespace" "message"="spec.certificateAuthorityData is invalid: illegal base64 data at input byte 7" "reason"="InvalidTLSConfig" "status"="False" "type"="OIDCDiscoverySucceeded"`,
+				`upstream-observer "error"="UpstreamOIDCProvider has a failing condition" "msg"="found failing condition" "message"="spec.certificateAuthorityData is invalid: illegal base64 data at input byte 7" "name"="test-name" "namespace"="test-namespace" "reason"="InvalidTLSConfig" "type"="OIDCDiscoverySucceeded"`,
+			},
+			wantResultingCache: []provider.UpstreamOIDCIdentityProvider{},
+			wantResultingUpstreams: []v1alpha1.UpstreamOIDCProvider{{
+				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
+				Status: v1alpha1.UpstreamOIDCProviderStatus{
+					Phase: "Error",
+					Conditions: []v1alpha1.Condition{
+						{
+							Type:               "ClientCredentialsValid",
+							Status:             "True",
+							LastTransitionTime: now,
+							Reason:             "Success",
+							Message:            "loaded client credentials",
+						},
+						{
+							Type:               "OIDCDiscoverySucceeded",
+							Status:             "False",
+							LastTransitionTime: now,
+							Reason:             "InvalidTLSConfig",
+							Message:            `spec.certificateAuthorityData is invalid: illegal base64 data at input byte 7`,
+						},
+					},
+				},
+			}},
+		},
+		{
+			name: "TLS CA bundle does not have any certificates",
+			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
+				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: "test-name"},
+				Spec: v1alpha1.UpstreamOIDCProviderSpec{
+					Issuer: testIssuerURL,
+					TLS: &v1alpha1.TLSSpec{
+						CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte("not-a-pem-ca-bundle")),
+					},
+					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
+					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: append(testAdditionalScopes, "xyz", "openid")},
+				},
+			}},
+			inputSecrets: []runtime.Object{&corev1.Secret{
+				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testSecretName},
+				Type:       "secrets.pinniped.dev/oidc-client",
+				Data:       testValidSecretData,
+			}},
+			wantErr: controllerlib.ErrSyntheticRequeue.Error(),
+			wantLogs: []string{
+				`upstream-observer "level"=0 "msg"="updated condition" "name"="test-name" "namespace"="test-namespace" "message"="loaded client credentials" "reason"="Success" "status"="True" "type"="ClientCredentialsValid"`,
+				`upstream-observer "level"=0 "msg"="updated condition" "name"="test-name" "namespace"="test-namespace" "message"="spec.certificateAuthorityData is invalid: no certificates found" "reason"="InvalidTLSConfig" "status"="False" "type"="OIDCDiscoverySucceeded"`,
+				`upstream-observer "error"="UpstreamOIDCProvider has a failing condition" "msg"="found failing condition" "message"="spec.certificateAuthorityData is invalid: no certificates found" "name"="test-name" "namespace"="test-namespace" "reason"="InvalidTLSConfig" "type"="OIDCDiscoverySucceeded"`,
+			},
+			wantResultingCache: []provider.UpstreamOIDCIdentityProvider{},
+			wantResultingUpstreams: []v1alpha1.UpstreamOIDCProvider{{
+				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
+				Status: v1alpha1.UpstreamOIDCProviderStatus{
+					Phase: "Error",
+					Conditions: []v1alpha1.Condition{
+						{
+							Type:               "ClientCredentialsValid",
+							Status:             "True",
+							LastTransitionTime: now,
+							Reason:             "Success",
+							Message:            "loaded client credentials",
+						},
+						{
+							Type:               "OIDCDiscoverySucceeded",
+							Status:             "False",
+							LastTransitionTime: now,
+							Reason:             "InvalidTLSConfig",
+							Message:            `spec.certificateAuthorityData is invalid: no certificates found`,
+						},
+					},
+				},
+			}},
+		},
 		{
 			name: "issuer is invalid URL",
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
@@ -240,7 +341,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL + "/invalid",
+					Issuer:              testIssuerURL + "/invalid",
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: testAdditionalScopes},
 				},
@@ -285,7 +387,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL + "/insecure",
+					Issuer:              testIssuerURL + "/insecure",
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: testAdditionalScopes},
 				},
@@ -330,7 +433,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: "test-name"},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL,
+					Issuer:              testIssuerURL,
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: append(testAdditionalScopes, "xyz", "openid")},
 				},
@@ -373,7 +477,8 @@ func TestController(t *testing.T) {
 			inputUpstreams: []runtime.Object{&v1alpha1.UpstreamOIDCProvider{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName, Generation: 1234},
 				Spec: v1alpha1.UpstreamOIDCProviderSpec{
-					Issuer:              testIssuer.URL,
+					Issuer:              testIssuerURL,
+					TLS:                 &v1alpha1.TLSSpec{CertificateAuthorityData: testIssuerCABase64},
 					Client:              v1alpha1.OIDCClient{SecretName: testSecretName},
 					AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{AdditionalScopes: testAdditionalScopes},
 				},
@@ -486,10 +591,9 @@ func normalizeUpstreams(upstreams []v1alpha1.UpstreamOIDCProvider, now metav1.Ti
 	return result
 }
 
-func newTestIssuer(t *testing.T) *httptest.Server {
+func newTestIssuer(t *testing.T) (string, string) {
 	mux := http.NewServeMux()
-	testServer := httptest.NewServer(mux)
+	caBundlePEM, testURL := testutil.TLSTestServer(t, mux.ServeHTTP)
-	t.Cleanup(testServer.Close)
 
 	type providerJSON struct {
 		Issuer   string `json:"issuer"`
@@ -502,7 +606,7 @@ func newTestIssuer(t *testing.T) *httptest.Server {
 	mux.HandleFunc("/.well-known/openid-configuration", func(w http.ResponseWriter, r *http.Request) {
 		w.Header().Set("content-type", "application/json")
 		_ = json.NewEncoder(w).Encode(&providerJSON{
-			Issuer:  testServer.URL,
+			Issuer:  testURL,
 			AuthURL: "https://example.com/authorize",
 		})
 	})
@@ -511,7 +615,7 @@ func newTestIssuer(t *testing.T) *httptest.Server {
 	mux.HandleFunc("/invalid/.well-known/openid-configuration", func(w http.ResponseWriter, r *http.Request) {
 		w.Header().Set("content-type", "application/json")
 		_ = json.NewEncoder(w).Encode(&providerJSON{
-			Issuer:  testServer.URL + "/invalid",
+			Issuer:  testURL + "/invalid",
 			AuthURL: "%",
 		})
 	})
@@ -520,10 +624,10 @@ func newTestIssuer(t *testing.T) *httptest.Server {
 	mux.HandleFunc("/insecure/.well-known/openid-configuration", func(w http.ResponseWriter, r *http.Request) {
 		w.Header().Set("content-type", "application/json")
 		_ = json.NewEncoder(w).Encode(&providerJSON{
-			Issuer:  testServer.URL + "/insecure",
+			Issuer:  testURL + "/insecure",
 			AuthURL: "http://example.com/authorize",
 		})
 	})
 
-	return testServer
+	return caBundlePEM, testURL
 }

internal/oidcclient/login.go

@@ -44,6 +44,8 @@ type handlerState struct {
 	scopes   []string
 	cache    SessionCache
 
+	httpClient *http.Client
+
 	// Parameters of the localhost listener.
 	listenAddr   string
 	callbackPath string
@@ -122,6 +124,14 @@ func WithSessionCache(cache SessionCache) Option {
 	}
 }
 
+// WithClient sets the HTTP client used to make CLI-to-provider requests.
+func WithClient(httpClient *http.Client) Option {
+	return func(h *handlerState) error {
+		h.httpClient = httpClient
+		return nil
+	}
+}
+
 // nopCache is a SessionCache that doesn't actually do anything.
 type nopCache struct{}
 
@@ -144,6 +154,7 @@ func Login(issuer string, clientID string, opts ...Option) (*Token, error) {
 		callbackPath: "/callback",
 		ctx:          context.Background(),
 		callbacks:    make(chan callbackResult),
+		httpClient:   http.DefaultClient,
 
 		// Default implementations of external dependencies (to be mocked in tests).
 		generateState: state.Generate,
@@ -163,6 +174,7 @@ func Login(issuer string, clientID string, opts ...Option) (*Token, error) {
 	// Always set a long, but non-infinite timeout for this operation.
 	ctx, cancel := context.WithTimeout(h.ctx, 10*time.Minute)
 	defer cancel()
+	ctx = oidc.ClientContext(ctx, h.httpClient)
 	h.ctx = ctx
 
 	// Initialize login parameters.

internal/oidcclient/login_test.go

@@ -416,6 +416,7 @@ func TestLogin(t *testing.T) {
 						require.Equal(t, []*Token{&testToken}, cache.sawPutTokens)
 					})
 					require.NoError(t, WithSessionCache(cache)(h))
+					require.NoError(t, WithClient(&http.Client{Timeout: 10 * time.Second})(h))
 
 					h.openURL = func(actualURL string) error {
 						parsedActualURL, err := url.Parse(actualURL)

test/deploy/dex/dex.yaml

@@ -6,13 +6,15 @@
 #@ load("@ytt:yaml", "yaml")
 
 #@ def dexConfig():
-issuer: http://dex.dex.svc.cluster.local/dex
+issuer: https://dex.dex.svc.cluster.local/dex
 storage:
   type: sqlite3
   config:
     file: ":memory:"
 web:
-  http: 0.0.0.0:80
+  https: 0.0.0.0:443
+  tlsCert: /var/certs/dex.pem
+  tlsKey: /var/certs/dex-key.pem
 oauth2:
   skipApprovalScreen: true
 staticClients:
@@ -67,24 +69,59 @@ spec:
       annotations:
         dexConfigHash: #@ sha256.sum(yaml.encode(dexConfig()))
     spec:
+      initContainers:
+      - name: generate-certs
+        image: cfssl/cfssl:1.5.0
+        imagePullPolicy: IfNotPresent
+        command: ["/bin/bash"]
+        args:
+        - -c
+        - |
+          cd /var/certs
+          cfssl print-defaults config > /tmp/cfssl-default.json
+          echo '{"CN": "Pinniped Test","hosts": [],"key": {"algo": "ecdsa","size": 256},"names": [{}]}' > csr.json
+
+          echo "generating CA key..."
+          cfssl genkey \
+            -config /tmp/cfssl-default.json \
+            -initca csr.json \
+            | cfssljson -bare ca
+
+          echo "generating Dex server certificate..."
+          cfssl gencert \
+            -ca ca.pem -ca-key ca-key.pem \
+            -config /tmp/cfssl-default.json \
+            -profile www \
+            -cn "dex.dex.svc.cluster.local" \
+            -hostname "dex.dex.svc.cluster.local" \
+            csr.json \
+            | cfssljson -bare dex
+        volumeMounts:
+          - name: certs
+            mountPath: /var/certs
       containers:
-        - name: dex
+      - name: dex
-          image: quay.io/dexidp/dex:v2.10.0
+        image: quay.io/dexidp/dex:v2.10.0
-          imagePullPolicy: IfNotPresent
+        imagePullPolicy: IfNotPresent
-          command:
+        command:
-          - /usr/local/bin/dex
+        - /usr/local/bin/dex
-          - serve
+        - serve
-          - /etc/dex/cfg/config.yaml
+        - /etc/dex/cfg/config.yaml
-          ports:
+        ports:
-          - name: http
+        - name: https
-            containerPort: 80
+          containerPort: 443
-          volumeMounts:
+        volumeMounts:
-          - name: config
+        - name: dex-config
-            mountPath: /etc/dex/cfg
+          mountPath: /etc/dex/cfg
+        - name: certs
+          mountPath: /var/certs
+          readOnly: true
       volumes:
-      - name: config
+      - name: dex-config
         configMap:
           name: dex-config
+      - name: certs
+        emptyDir: {}
 ---
 apiVersion: v1
 kind: Service
@@ -98,4 +135,5 @@ spec:
   selector:
     app: dex
   ports:
-    - port: 80
+  - port: 443
+    name: https

test/integration/cli_test.go

@@ -130,8 +130,8 @@ func getLoginProvider(t *testing.T) *loginProviderPatterns {
 		},
 		{
 			Name:                "Dex",
-			IssuerPattern:       regexp.MustCompile(`\Ahttp://dex\.dex\.svc\.cluster\.local/dex.*\z`),
+			IssuerPattern:       regexp.MustCompile(`\Ahttps://dex\.dex\.svc\.cluster\.local/dex.*\z`),
-			LoginPagePattern:    regexp.MustCompile(`\Ahttp://dex\.dex\.svc\.cluster\.local/dex/auth/local.+\z`),
+			LoginPagePattern:    regexp.MustCompile(`\Ahttps://dex\.dex\.svc\.cluster\.local/dex/auth/local.+\z`),
 			UsernameSelector:    "input#login",
 			PasswordSelector:    "input#password",
 			LoginButtonSelector: "button#submit-login",
@@ -170,6 +170,7 @@ func TestCLILoginOIDC(t *testing.T) {
 		agouti.Desired(caps),
 		agouti.ChromeOptions("args", []string{
 			"--no-sandbox",
+			"--ignore-certificate-errors",
 			"--headless", // Comment out this line to see the tests happen in a visible browser window.
 		}),
 		// Uncomment this to see stdout/stderr from chromedriver.
@@ -413,6 +414,15 @@ func oidcLoginCommand(ctx context.Context, t *testing.T, pinnipedExe string, ses
 		"--session-cache", sessionCachePath,
 		"--skip-browser",
 	)
+
+	// If there is a custom CA bundle, pass it via --ca-bundle and a temporary file.
+	if env.OIDCUpstream.CABundle != "" {
+		path := filepath.Join(t.TempDir(), "test-ca.pem")
+		require.NoError(t, ioutil.WriteFile(path, []byte(env.OIDCUpstream.CABundle), 0600))
+		cmd.Args = append(cmd.Args, "--ca-bundle", path)
+	}
+
+	// If there is a custom proxy, set it using standard environment variables.
 	if env.Proxy != "" {
 		cmd.Env = append(os.Environ(),
 			"http_proxy="+env.Proxy,

test/integration/supervisor_upstream_test.go

@@ -5,6 +5,7 @@ package integration
 
 import (
 	"context"
+	"encoding/base64"
 	"testing"
 	"time"
 
@@ -17,7 +18,7 @@ import (
 )
 
 func TestSupervisorUpstreamOIDCDiscovery(t *testing.T) {
-	library.SkipUnlessIntegration(t)
+	env := library.IntegrationEnv(t)
 
 	t.Run("invalid missing secret and bad issuer", func(t *testing.T) {
 		t.Parallel()
@@ -50,7 +51,10 @@ func TestSupervisorUpstreamOIDCDiscovery(t *testing.T) {
 	t.Run("valid", func(t *testing.T) {
 		t.Parallel()
 		spec := v1alpha1.UpstreamOIDCProviderSpec{
-			Issuer: "https://accounts.google.com", // Use Google as an example of a valid OIDC issuer for now.
+			Issuer: env.OIDCUpstream.Issuer,
+			TLS: &v1alpha1.TLSSpec{
+				CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte(env.OIDCUpstream.CABundle)),
+			},
 			AuthorizationConfig: v1alpha1.OIDCAuthorizationConfig{
 				AdditionalScopes: []string{"email", "profile"},
 			},

test/library/env.go

@@ -48,6 +48,7 @@ type TestEnv struct {
 
 	OIDCUpstream struct {
 		Issuer        string `json:"issuer"`
+		CABundle      string `json:"caBundle" `
 		ClientID      string `json:"clientID"`
 		LocalhostPort int    `json:"localhostPort"`
 		Username      string `json:"username"`
@@ -130,6 +131,7 @@ func loadEnvVars(t *testing.T, result *TestEnv) {
 	result.Proxy = os.Getenv("PINNIPED_TEST_PROXY")
 
 	result.OIDCUpstream.Issuer = needEnv(t, "PINNIPED_TEST_CLI_OIDC_ISSUER")
+	result.OIDCUpstream.CABundle = os.Getenv("PINNIPED_TEST_CLI_OIDC_ISSUER_CA_BUNDLE")
 	result.OIDCUpstream.ClientID = needEnv(t, "PINNIPED_TEST_CLI_OIDC_CLIENT_ID")
 	result.OIDCUpstream.LocalhostPort, _ = strconv.Atoi(needEnv(t, "PINNIPED_TEST_CLI_OIDC_LOCALHOST_PORT"))
 	result.OIDCUpstream.Username = needEnv(t, "PINNIPED_TEST_CLI_OIDC_USERNAME")