diff --git a/pkg/auth/monitored_token_source.go b/pkg/auth/monitored_token_source.go
index 5f3ed4c431..b0d075302c 100644
--- a/pkg/auth/monitored_token_source.go
+++ b/pkg/auth/monitored_token_source.go
@@ -11,6 +11,7 @@ import (
 	"net"
 	"os"
 	"strconv"
+	"strings"
 	"sync"
 	"syscall"
 	"time"
@@ -173,10 +174,11 @@ func (mts *MonitoredTokenSource) Stopped() <-chan struct{} {
 	return mts.stopped
 }
 
-// Token retrieves a token, retrying with exponential backoff on transient network
-// errors (DNS failures, TCP errors). On non-transient errors (OAuth 4xx, TLS failures)
-// it marks the workload as unauthenticated and returns immediately. Context cancellation
-// (workload removal) stops the retry without marking the workload as unauthenticated.
+// Token retrieves a token, retrying with exponential backoff on transient errors
+// (see isTransientNetworkError for the full list). On non-transient errors
+// (OAuth 4xx, TLS failures) it marks the workload as unauthenticated and returns
+// immediately. Context cancellation (workload removal) stops the retry without
+// marking the workload as unauthenticated.
 //
 // Concurrent callers are deduplicated via singleflight so that only one retry
 // loop runs at a time during transient failures.
@@ -322,20 +324,39 @@ func (mts *MonitoredTokenSource) onTick() (bool, time.Duration) {
 	return false, wait
 }
 
-// isTransientNetworkError reports whether err represents a transient network condition
-// (DNS failure, TCP transport error, timeout) that is likely to resolve when the network
-// recovers — for example, after a VPN reconnects.
+// isTransientNetworkError reports whether err represents a transient condition
+// (DNS failure, TCP transport error, timeout, OAuth server 5xx, unparsable
+// token response) that is likely to resolve on its own.
 //
-// OAuth2 HTTP-level auth failures (invalid_grant, 401, 400) and TLS errors
+// OAuth2 client-level auth failures (invalid_grant, 401, 400) and TLS errors
 // (certificate verification, handshake failure) are NOT considered transient and
 // return false so the workload is marked unauthenticated immediately.
 func isTransientNetworkError(err error) bool {
 	if err == nil ||
-		errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) ||
-		errors.As(err, new(*oauth2.RetrieveError)) {
+		errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) {
 		return false
 	}
 
+	// OAuth HTTP-level errors: 5xx (Bad Gateway, Service Unavailable, Gateway
+	// Timeout) are transient server-side issues that typically resolve on their
+	// own. 4xx errors (invalid_grant, invalid_client) are permanent auth failures.
+	if retrieveErr, ok := errors.AsType[*oauth2.RetrieveError](err); ok {
+		if retrieveErr.Response != nil && retrieveErr.Response.StatusCode >= 500 {
+			slog.Debug("treating OAuth server error as transient",
+				"status_code", retrieveErr.Response.StatusCode,
+			)
+			return true
+		}
+		return false
+	}
+
+	// Non-JSON responses from the OAuth server (e.g. load balancer HTML pages).
+	// The oauth2 library returns a plain error (not *RetrieveError) when the
+	// HTTP status is 2xx but the body cannot be parsed as JSON.
+	if isOAuthParseError(err) {
+		return true
+	}
+
 	// DNS lookup failures — covers VPN-disconnect scenarios where the corporate DNS
 	// resolver is unreachable.
 	if _, ok := errors.AsType[*net.DNSError](err); ok {
@@ -360,6 +381,21 @@ func isTransientNetworkError(err error) bool {
 	return false
 }
 
+// isOAuthParseError detects errors from the oauth2 library that indicate the
+// token endpoint returned an unparsable response body on a 2xx status. This
+// typically happens when a load balancer, CDN, or reverse proxy intercepts the
+// request and returns its own HTML page instead of the expected JSON token
+// response. The oauth2 library uses fmt.Errorf with %v (not %w) for these
+// errors, so string matching is the only reliable detection method.
+func isOAuthParseError(err error) bool {
+	if err == nil {
+		return false
+	}
+	msg := err.Error()
+	return strings.Contains(msg, "oauth2: cannot parse json") ||
+		strings.Contains(msg, "oauth2: cannot parse response")
+}
+
 // markAsUnauthenticated marks the workload as unauthenticated and stops background monitoring.
 func (mts *MonitoredTokenSource) markAsUnauthenticated(reason string) {
 	_ = mts.statusUpdater.SetWorkloadStatus(
diff --git a/pkg/auth/monitored_token_source_test.go b/pkg/auth/monitored_token_source_test.go
index 342082820a..9a2fa527f0 100644
--- a/pkg/auth/monitored_token_source_test.go
+++ b/pkg/auth/monitored_token_source_test.go
@@ -6,6 +6,7 @@ package auth
 import (
 	"context"
 	"errors"
+	"fmt"
 	"net"
 	"net/http"
 	"net/url"
@@ -561,11 +562,21 @@ func TestMonitoredTokenSource_BackgroundMonitor_ErrorClassification(t *testing.T
 		{name: "context.DeadlineExceeded", err: context.DeadlineExceeded, isTransient: false},
 		{name: "oauth2.RetrieveError 401", err: createRetrieveError(http.StatusUnauthorized, "unauthorized"), isTransient: false},
 		{name: "oauth2.RetrieveError 400 invalid_grant", err: createRetrieveError(http.StatusBadRequest, "invalid_grant"), isTransient: false},
+		{name: "oauth2.RetrieveError nil response", err: &oauth2.RetrieveError{}, isTransient: false},
 		// Transient: network-level errors must be retried.
 		{name: "*net.DNSError timeout", err: &net.DNSError{Err: "i/o timeout", Name: "example.com", IsTimeout: true}, isTransient: true},
 		{name: "*net.OpError connection refused", err: &net.OpError{Op: "dial", Net: "tcp", Err: &os.SyscallError{Syscall: "connect", Err: syscall.ECONNREFUSED}}, isTransient: true},
 		{name: "*url.Error wrapping *net.OpError", err: &url.Error{Op: "Post", URL: "https://example.com/token", Err: &net.OpError{Op: "dial", Net: "tcp", Err: &os.SyscallError{Syscall: "connect", Err: syscall.ECONNREFUSED}}}, isTransient: true},
 		{name: "net.Error timeout", err: &timeoutNetError{}, isTransient: true},
+		// Transient: OAuth server 5xx errors (load balancer, server restart).
+		{name: "oauth2.RetrieveError 500", err: createRetrieveError(http.StatusInternalServerError, "Internal Server Error"), isTransient: true},
+		{name: "oauth2.RetrieveError 502", err: createRetrieveError(http.StatusBadGateway, "Bad Gateway"), isTransient: true},
+		{name: "oauth2.RetrieveError 503", err: createRetrieveError(http.StatusServiceUnavailable, "Service Unavailable"), isTransient: true},
+		{name: "oauth2.RetrieveError 504", err: createRetrieveError(http.StatusGatewayTimeout, "Gateway Timeout"), isTransient: true},
+		// Transient: unparsable OAuth responses (HTML from load balancer on 200).
+		{name: "oauth2 cannot parse json", err: fmt.Errorf("oauth2: cannot parse json: invalid character '<'"), isTransient: true},
+		{name: "wrapped oauth2 parse error", err: fmt.Errorf("refresh failed: %w", fmt.Errorf("oauth2: cannot parse json: invalid character '<'")), isTransient: true},
+		{name: "oauth2 cannot parse response", err: fmt.Errorf("oauth2: cannot parse response: invalid URL escape"), isTransient: true},
 	}
 
 	for _, tt := range tests {