diff --git a/app/src/main/java/eu/kanade/tachiyomi/data/track/myanimelist/MyAnimeListInterceptor.kt b/app/src/main/java/eu/kanade/tachiyomi/data/track/myanimelist/MyAnimeListInterceptor.kt
index da1768178..16313520c 100644
--- a/app/src/main/java/eu/kanade/tachiyomi/data/track/myanimelist/MyAnimeListInterceptor.kt
+++ b/app/src/main/java/eu/kanade/tachiyomi/data/track/myanimelist/MyAnimeListInterceptor.kt
@@ -20,23 +20,9 @@ class MyAnimeListInterceptor(private val myanimelist: MyAnimeList, private var t
         }
         // Refresh access token if expired
         if (oauth != null && oauth!!.isExpired()) {
-            val newOauth = runCatching {
-                val oauthResponse = chain.proceed(MyAnimeListApi.refreshTokenRequest(oauth!!))
-
-                if (oauthResponse.isSuccessful) {
-                    oauthResponse.parseAs<OAuth>()
-                } else {
-                    oauthResponse.close()
-                    null
-                }
-            }
-
-            if (newOauth.getOrNull() == null) {
-                throw IOException("Failed to refresh the access token")
-            }
-
-            setAuth(newOauth.getOrNull())
+            setAuth(refreshToken(chain))
         }
+
         if (oauth == null) {
             throw IOException("No authentication token")
         }
@@ -46,7 +32,26 @@ class MyAnimeListInterceptor(private val myanimelist: MyAnimeList, private var t
             .addHeader("Authorization", "Bearer ${oauth!!.access_token}")
             .build()
 
-        return chain.proceed(authRequest)
+        val response = chain.proceed(authRequest)
+        val tokenIsExpired = response.headers["www-authenticate"]
+            ?.contains("The access token expired") ?: false
+
+        // Retry the request once with a new token in case it was not already refreshed
+        // by the is expired check before.
+        if (response.code == 401 && tokenIsExpired) {
+            response.close()
+
+            val newToken = refreshToken(chain)
+            setAuth(newToken)
+
+            val newRequest = originalRequest.newBuilder()
+                .addHeader("Authorization", "Bearer ${newToken.access_token}")
+                .build()
+
+            return chain.proceed(newRequest)
+        }
+
+        return response
     }
 
     /**
@@ -58,4 +63,23 @@ class MyAnimeListInterceptor(private val myanimelist: MyAnimeList, private var t
         this.oauth = oauth
         myanimelist.saveOAuth(oauth)
     }
+
+    private fun refreshToken(chain: Interceptor.Chain): OAuth {
+        val newOauth = runCatching {
+            val oauthResponse = chain.proceed(MyAnimeListApi.refreshTokenRequest(oauth!!))
+
+            if (oauthResponse.isSuccessful) {
+                oauthResponse.parseAs<OAuth>()
+            } else {
+                oauthResponse.close()
+                null
+            }
+        }
+
+        if (newOauth.getOrNull() == null) {
+            throw IOException("Failed to refresh the access token")
+        }
+
+        return newOauth.getOrNull()!!
+    }
 }