diff --git a/lib/resource-mapper.js b/lib/resource-mapper.js
index 54514cfa6..0d21eeb42 100644
--- a/lib/resource-mapper.js
+++ b/lib/resource-mapper.js
@@ -4,6 +4,7 @@ const { promisify } = require('util')
 const { types, extensions } = require('mime-types')
 const readdir = promisify(fs.readdir)
 const HTTPError = require('./http-error')
+const pathUtil = require('path')
 
 /*
  * A ResourceMapper maintains the mapping between HTTP URLs and server filenames,
@@ -78,7 +79,9 @@ class ResourceMapper {
 
     // Determine the URL by chopping off everything after the dollar sign
     const pathname = this._removeDollarExtension(path)
-    const url = `${this.resolveUrl(hostname)}${encodeURI(pathname)}`
+    const url = `${this.resolveUrl(hostname)}${
+      pathname.split(pathUtil.sep).map((component) => encodeURIComponent(component)).join('/')
+    }`
     return { url, contentType: this._getContentTypeFromExtension(path) }
   }
 
diff --git a/test/unit/resource-mapper-test.js b/test/unit/resource-mapper-test.js
index b0c7b7630..65d66a58a 100644
--- a/test/unit/resource-mapper-test.js
+++ b/test/unit/resource-mapper-test.js
@@ -489,6 +489,13 @@ describe('ResourceMapper', () => {
         url: 'http://localhost/space/foo%20bar%20bar.html',
         contentType: 'text/html'
       })
+
+    itMapsFile(mapper, 'a file with even stranger disallowed IRI characters',
+      { path: `${rootPath}space/Blog discovery for the future? · Issue #96 · scripting:Scripting-News · GitHub.pdf` },
+      {
+        url: 'http://localhost/space/Blog%20discovery%20for%20the%20future%3F%20%C2%B7%20Issue%20%2396%20%C2%B7%20scripting%3AScripting-News%20%C2%B7%20GitHub.pdf',
+        contentType: 'application/pdf'
+      })
   })
 
   describe('A ResourceMapper instance for a multi-host setup', () => {