diff --git a/apps/server/src/routes/custom.ts b/apps/server/src/routes/custom.ts
index e4494a6cd..b27a710f2 100644
--- a/apps/server/src/routes/custom.ts
+++ b/apps/server/src/routes/custom.ts
@@ -5,7 +5,7 @@ import cls from "../services/cls.js";
 import sql from "../services/sql.js";
 import becca from "../becca/becca.js";
 import type { Request, Response, Router } from "express";
-import { safeExtractMessageAndStackFromError } from "../services/utils.js";
+import { safeExtractMessageAndStackFromError, normalizeCustomHandlerPattern } from "../services/utils.js";
 
 function handleRequest(req: Request, res: Response) {
 
@@ -38,11 +38,19 @@ function handleRequest(req: Request, res: Response) {
             continue;
         }
 
-        const regex = new RegExp(`^${attr.value}$`);
-        let match;
+        // Get normalized patterns to handle both trailing slash cases
+        const patterns = normalizeCustomHandlerPattern(attr.value);
+        let match: RegExpMatchArray | null = null;
 
         try {
-            match = path.match(regex);
+            // Try each pattern until we find a match
+            for (const pattern of patterns) {
+                const regex = new RegExp(`^${pattern}$`);
+                match = path.match(regex);
+                if (match) {
+                    break; // Found a match, exit pattern loop
+                }
+            }
         } catch (e: unknown) {
             const [errMessage, errStack] = safeExtractMessageAndStackFromError(e);
             log.error(`Testing path for label '${attr.attributeId}', regex '${attr.value}' failed with error: ${errMessage}, stack: ${errStack}`);
diff --git a/apps/server/src/services/sync_options.ts b/apps/server/src/services/sync_options.ts
index 289323b54..657c1b214 100644
--- a/apps/server/src/services/sync_options.ts
+++ b/apps/server/src/services/sync_options.ts
@@ -2,6 +2,7 @@
 
 import optionService from "./options.js";
 import config from "./config.js";
+import { normalizeUrl } from "./utils.js";
 
 /*
  * Primary configuration for sync is in the options (document), but we allow to override
@@ -17,7 +18,10 @@ function get(name: keyof typeof config.Sync) {
 export default {
     // env variable is the easiest way to guarantee we won't overwrite prod data during development
     // after copying prod document/data directory
-    getSyncServerHost: () => get("syncServerHost"),
+    getSyncServerHost: () => {
+        const host = get("syncServerHost");
+        return host ? normalizeUrl(host) : host;
+    },
     isSyncSetup: () => {
         const syncServerHost = get("syncServerHost");
 
diff --git a/apps/server/src/services/utils.spec.ts b/apps/server/src/services/utils.spec.ts
index f6b21a8cd..6e027b7bd 100644
--- a/apps/server/src/services/utils.spec.ts
+++ b/apps/server/src/services/utils.spec.ts
@@ -628,3 +628,56 @@ describe("#formatDownloadTitle", () => {
         });
     });
 });
+
+describe("#normalizeUrl", () => {
+    const testCases: TestCase<typeof utils.normalizeUrl>[] = [
+        [ "should remove trailing slash from simple URL", [ "https://example.com/" ], "https://example.com" ],
+        [ "should remove trailing slash from URL with path", [ "https://example.com/path/" ], "https://example.com/path" ],
+        [ "should preserve URL without trailing slash", [ "https://example.com" ], "https://example.com" ],
+        [ "should preserve URL without trailing slash with path", [ "https://example.com/path" ], "https://example.com/path" ],
+        [ "should preserve protocol-only URLs", [ "https://" ], "https://" ],
+        [ "should preserve protocol-only URLs", [ "http://" ], "http://" ],
+        [ "should fix double slashes in path", [ "https://example.com//api//test" ], "https://example.com/api/test" ],
+        [ "should handle multiple double slashes", [ "https://example.com///api///test" ], "https://example.com/api/test" ],
+        [ "should handle trailing slash with double slashes", [ "https://example.com//api//" ], "https://example.com/api" ],
+        [ "should preserve protocol double slash", [ "https://example.com/api" ], "https://example.com/api" ],
+        [ "should handle empty string", [ "" ], "" ],
+        [ "should handle whitespace-only string", [ "   " ], "" ],
+        [ "should trim whitespace", [ " https://example.com/ " ], "https://example.com" ],
+        [ "should handle null as empty", [ null as any ], null ],
+        [ "should handle undefined as empty", [ undefined as any ], undefined ]
+    ];
+
+    testCases.forEach((testCase) => {
+        const [ desc, fnParams, expected ] = testCase;
+        it(desc, () => {
+            const result = utils.normalizeUrl(...fnParams);
+            expect(result).toStrictEqual(expected);
+        });
+    });
+});
+
+describe("#normalizeCustomHandlerPattern", () => {
+    const testCases: TestCase<typeof utils.normalizeCustomHandlerPattern>[] = [
+        [ "should handle pattern without ending - add both versions", [ "foo" ], [ "foo", "foo/" ] ],
+        [ "should handle pattern with trailing slash - add both versions", [ "foo/" ], [ "foo", "foo/" ] ],
+        [ "should handle pattern ending with $ - add optional slash", [ "foo$" ], [ "foo/?$" ] ],
+        [ "should handle pattern with trailing slash and $ - add both versions", [ "foo/$" ], [ "foo$", "foo/$" ] ],
+        [ "should preserve existing optional slash pattern", [ "foo/?$" ], [ "foo/?$" ] ],
+        [ "should preserve existing optional slash pattern (alternative)", [ "foo/?)" ], [ "foo/?)" ] ],
+        [ "should handle regex pattern with special chars", [ "api/[a-z]+$" ], [ "api/[a-z]+/?$" ] ],
+        [ "should handle complex regex pattern", [ "user/([0-9]+)/profile$" ], [ "user/([0-9]+)/profile/?$" ] ],
+        [ "should handle empty string", [ "" ], [ "" ] ],
+        [ "should handle whitespace-only string", [ "   " ], [ "" ] ],
+        [ "should handle null", [ null as any ], [ null ] ],
+        [ "should handle undefined", [ undefined as any ], [ undefined ] ]
+    ];
+
+    testCases.forEach((testCase) => {
+        const [ desc, fnParams, expected ] = testCase;
+        it(desc, () => {
+            const result = utils.normalizeCustomHandlerPattern(...fnParams);
+            expect(result).toStrictEqual(expected);
+        });
+    });
+});
diff --git a/apps/server/src/services/utils.ts b/apps/server/src/services/utils.ts
index 89aad1bbb..5d5559d25 100644
--- a/apps/server/src/services/utils.ts
+++ b/apps/server/src/services/utils.ts
@@ -375,6 +375,85 @@ export function safeExtractMessageAndStackFromError(err: unknown): [errMessage:
     return (err instanceof Error) ? [err.message, err.stack] as const : ["Unknown Error", undefined] as const;
 }
 
+/**
+ * Normalizes URL by removing trailing slashes and fixing double slashes.
+ * Preserves the protocol (http://, https://) but removes trailing slashes from the rest.
+ * 
+ * @param url The URL to normalize
+ * @returns The normalized URL without trailing slashes
+ */
+export function normalizeUrl(url: string | null | undefined): string | null | undefined {
+    if (!url || typeof url !== 'string') {
+        return url;
+    }
+
+    // Trim whitespace
+    url = url.trim();
+    
+    if (!url) {
+        return url;
+    }
+
+    // Fix double slashes (except in protocol) first
+    url = url.replace(/([^:]\/)\/+/g, '$1');
+    
+    // Remove trailing slash, but preserve protocol
+    if (url.endsWith('/') && !url.match(/^https?:\/\/$/)) {
+        url = url.slice(0, -1);
+    }
+    
+    return url;
+}
+
+/**
+ * Normalizes a path pattern for custom request handlers.
+ * Ensures both trailing slash and non-trailing slash versions are handled.
+ * 
+ * @param pattern The original pattern from customRequestHandler attribute
+ * @returns An array of patterns to match both with and without trailing slash
+ */
+export function normalizeCustomHandlerPattern(pattern: string | null | undefined): (string | null | undefined)[] {
+    if (!pattern || typeof pattern !== 'string') {
+        return [pattern];
+    }
+
+    pattern = pattern.trim();
+    
+    if (!pattern) {
+        return [pattern];
+    }
+
+    // If pattern already ends with optional trailing slash, return as-is
+    if (pattern.endsWith('/?$') || pattern.endsWith('/?)')) {
+        return [pattern];
+    }
+
+    // If pattern ends with $, handle it specially
+    if (pattern.endsWith('$')) {
+        const basePattern = pattern.slice(0, -1);
+        
+        // If already ends with slash, create both versions
+        if (basePattern.endsWith('/')) {
+            const withoutSlash = basePattern.slice(0, -1) + '$';
+            const withSlash = pattern;
+            return [withoutSlash, withSlash];
+        } else {
+            // Add optional trailing slash
+            const withSlash = basePattern + '/?$';
+            return [withSlash];
+        }
+    }
+
+    // For patterns without $, add both versions
+    if (pattern.endsWith('/')) {
+        const withoutSlash = pattern.slice(0, -1);
+        return [withoutSlash, pattern];
+    } else {
+        const withSlash = pattern + '/';
+        return [pattern, withSlash];
+    }
+}
+
 
 export default {
     compareVersions,
@@ -400,6 +479,8 @@ export default {
     md5,
     newEntityId,
     normalize,
+    normalizeCustomHandlerPattern,
+    normalizeUrl,
     quoteRegex,
     randomSecureToken,
     randomString,