diff --git a/DevProxy.Integration.Tests/GraphUtilsTests.cs b/DevProxy.Integration.Tests/GraphUtilsTests.cs
new file mode 100644
index 00000000..17d6919f
--- /dev/null
+++ b/DevProxy.Integration.Tests/GraphUtilsTests.cs
@@ -0,0 +1,100 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using DevProxy.Plugins.Utils;
+using Xunit;
+
+namespace DevProxy.Integration.Tests;
+
+public class GraphUtilsTests
+{
+    [Theory]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/drive/root:/Documents/report.xlsx:/workbook/worksheets",
+        "/me/drive/items/{id}/workbook/worksheets")]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/drives/drive-id/root:/Documents/report.xlsx",
+        "/drives/{drives-id}/items/{id}")]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/groups/group-id/drive/root:/Documents/report.xlsx:/content",
+        "/groups/{groups-id}/drive/items/{id}/content")]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/me/drive/root:/Documents/report.xlsx:/permissions",
+        "/me/drive/items/{id}/permissions")]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/sites/{site-id}/drive/root:/Documentos/informe.pdf:/content",
+        "/sites/{site-id}/drive/items/{id}/content")]
+    [InlineData(
+        "https://graph.microsoft.com/beta/users/user-id/drive/root:/Documents/report.xlsx:/children",
+        "/users/{users-id}/drive/items/{id}/children")]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/drives/drive-id/items/parent-id:/Documents/report.xlsx:/createUploadSession",
+        "/drives/{drives-id}/items/{id}/createUploadSession")]
+    public void GetTokenizedUrl_RootRelativePath_ReturnsIdAddressedUrl(string url, string expected) =>
+        Assert.Equal(expected, GraphUtils.GetTokenizedUrl(url));
+
+    [Theory]
+    [InlineData("My%20Files/quarterly-report%20%231.xlsx")]
+    [InlineData("O'Brien/estimate%25s.xlsx")]
+    [InlineData("Break%23Out/saved_game%5B1%5D.bin")]
+    public void GetTokenizedUrl_PathWithSpecialCharacters_ReturnsIdAddressedUrl(string itemPath)
+    {
+        var url = $"https://graph.microsoft.com/v1.0/me/drive/root:/{itemPath}:/content";
+
+        Assert.Equal("/me/drive/items/{id}/content", GraphUtils.GetTokenizedUrl(url));
+    }
+
+    [Theory]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/me/drive/items/parent-id:/Documents/report.txt:/content",
+        "/me/drive/items/{id}/content")]
+    [InlineData(
+        "https://graph.microsoft.com/v1.0/me/drive/special/documents:/report.txt:/content",
+        "/me/drive/items/{id}/content")]
+    public void GetTokenizedUrl_ItemRelativePath_ReturnsIdAddressedUrl(string url, string expected) =>
+        Assert.Equal(expected, GraphUtils.GetTokenizedUrl(url));
+
+    [Fact]
+    public void GetTokenizedUrl_NonPathAddressedUrl_PreservesExistingTokenization() =>
+        Assert.Equal(
+            "/sites/{sites-id}/drive/items/{items-id}/content",
+            GraphUtils.GetTokenizedUrl("https://graph.microsoft.com/v1.0/sites/site-id/drive/items/item-id/content"));
+
+    [Fact]
+    public void GetRequestsFromBatch_PathAddressedRequest_ReturnsIdAddressedUrl()
+    {
+        const string batchBody =
+            """
+            {
+              "requests": [
+                {
+                  "id": "1",
+                  "method": "PUT",
+                  "url": "/sites/site-id/drive/root:/Documents/report.txt:/content"
+                },
+                {
+                  "id": "2",
+                  "method": "GET",
+                  "url": "/sites/site-id/drive/items/item-id"
+                }
+              ]
+            }
+            """;
+
+        var requests = GraphUtils.GetRequestsFromBatch(batchBody, "v1.0", "graph.microsoft.com");
+
+        Assert.Collection(
+            requests,
+            request =>
+            {
+                Assert.Equal("PUT", request.Method);
+                Assert.Equal("/sites/{sites-id}/drive/items/{id}/content", request.Url);
+            },
+            request =>
+            {
+                Assert.Equal("GET", request.Method);
+                Assert.Equal("/sites/{sites-id}/drive/items/{items-id}", request.Url);
+            });
+    }
+}
diff --git a/DevProxy.Plugins/Utils/GraphUtils.cs b/DevProxy.Plugins/Utils/GraphUtils.cs
index b5bed771..d06547c8 100644
--- a/DevProxy.Plugins/Utils/GraphUtils.cs
+++ b/DevProxy.Plugins/Utils/GraphUtils.cs
@@ -9,6 +9,7 @@
 using Microsoft.Extensions.Logging;
 using System.Net.Http.Json;
 using System.Text.Json;
+using System.Text.RegularExpressions;
 
 namespace DevProxy.Plugins.Utils;
 
@@ -16,6 +17,10 @@ sealed class GraphUtils(
     HttpClient httpClient,
     ILogger<GraphUtils> logger)
 {
+    private static readonly Regex DriveItemPathRegex = new(
+        @"^/(?<version>v1\.0|beta)/(?<drive>drive|drives/[^/]+|groups/[^/]+/drive|me/drive|sites/[^/]+/drive|users/[^/]+/drive)/(?:root|items/[^/]+|special/[^/]+):/",
+        RegexOptions.IgnoreCase);
+
     private readonly HttpClient _httpClient = httpClient;
     private readonly ILogger _logger = logger;
 
@@ -115,10 +120,33 @@ internal async Task<IEnumerable<string>> UpdateUserScopesAsync(IEnumerable<strin
 
     internal static string GetTokenizedUrl(string absoluteUrl)
     {
+        absoluteUrl = CanonicalizeDriveItemPathUrl(absoluteUrl);
         var sanitizedUrl = ProxyUtils.SanitizeUrl(absoluteUrl);
         return "/" + string.Concat(new Uri(sanitizedUrl).Segments.Skip(2).Select(Uri.UnescapeDataString));
     }
 
+    private static string CanonicalizeDriveItemPathUrl(string absoluteUrl)
+    {
+        var uri = new Uri(absoluteUrl);
+        var path = Uri.UnescapeDataString(uri.AbsolutePath);
+        var match = DriveItemPathRegex.Match(path);
+        if (!match.Success)
+        {
+            return absoluteUrl;
+        }
+
+        var suffixDelimiterIndex = path.IndexOf(":/", match.Index + match.Length, StringComparison.Ordinal);
+        var suffix = suffixDelimiterIndex < 0 ? string.Empty : path[(suffixDelimiterIndex + 1)..];
+        var drive = match.Groups["drive"].Value;
+        if (drive.Equals("drive", StringComparison.OrdinalIgnoreCase))
+        {
+            drive = "me/drive";
+        }
+
+        var canonicalPath = $"/{match.Groups["version"].Value}/{drive}/items/{{id}}{suffix}";
+        return $"{uri.GetLeftPart(UriPartial.Authority)}{canonicalPath}{uri.Query}";
+    }
+
     internal static MethodAndUrl[] GetRequestsFromBatch(string batchBody, string graphVersion, string graphHostName)
     {
         var requests = new List<MethodAndUrl>();