diff --git a/pkg/apis/options/legacy_options.go b/pkg/apis/options/legacy_options.go
index 157487a..a2256da 100644
--- a/pkg/apis/options/legacy_options.go
+++ b/pkg/apis/options/legacy_options.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"net/url"
 	"strconv"
+	"strings"
 	"time"
 
 	"github.com/oauth2-proxy/oauth2-proxy/pkg/logger"
@@ -87,6 +88,8 @@ func (l *LegacyUpstreams) convert() (Upstreams, error) {
 			if u.Fragment != "" {
 				upstream.ID = u.Fragment
 				upstream.Path = u.Fragment
+				// Trim the fragment from the end of the URI
+				upstream.URI = strings.SplitN(upstreamString, "#", 2)[0]
 			}
 		case "static":
 			responseCode, err := strconv.Atoi(u.Host)
diff --git a/pkg/apis/options/legacy_options_test.go b/pkg/apis/options/legacy_options_test.go
index 5819e4b..80ad17b 100644
--- a/pkg/apis/options/legacy_options_test.go
+++ b/pkg/apis/options/legacy_options_test.go
@@ -21,7 +21,7 @@ var _ = Describe("Legacy Options", func() {
 			legacyOpts.LegacyUpstreams.PassHostHeader = true
 			legacyOpts.LegacyUpstreams.ProxyWebSockets = true
 			legacyOpts.LegacyUpstreams.SSLUpstreamInsecureSkipVerify = true
-			legacyOpts.LegacyUpstreams.Upstreams = []string{"http://foo.bar/baz", "file://var/lib/website#/bar", "static://204"}
+			legacyOpts.LegacyUpstreams.Upstreams = []string{"http://foo.bar/baz", "file:///var/lib/website#/bar", "static://204"}
 
 			truth := true
 			staticCode := 204
@@ -38,7 +38,7 @@ var _ = Describe("Legacy Options", func() {
 				{
 					ID:                    "/bar",
 					Path:                  "/bar",
-					URI:                   "file://var/lib/website#/bar",
+					URI:                   "file:///var/lib/website",
 					FlushInterval:         &flushInterval,
 					InsecureSkipTLSVerify: true,
 					PassHostHeader:        &truth,
@@ -100,11 +100,11 @@ var _ = Describe("Legacy Options", func() {
 			FlushInterval:         &flushInterval,
 		}
 
-		validFileWithFragment := "file://var/lib/website#/bar"
+		validFileWithFragment := "file:///var/lib/website#/bar"
 		validFileWithFragmentUpstream := Upstream{
 			ID:                    "/bar",
 			Path:                  "/bar",
-			URI:                   validFileWithFragment,
+			URI:                   "file:///var/lib/website",
 			InsecureSkipTLSVerify: skipVerify,
 			PassHostHeader:        &passHostHeader,
 			ProxyWebSockets:       &proxyWebSockets,