diff --git a/httpclient5/src/main/java/org/apache/hc/client5/http/impl/RequestSupport.java b/httpclient5/src/main/java/org/apache/hc/client5/http/impl/RequestSupport.java
index 5a8cde1ffb..9beb5f0054 100644
--- a/httpclient5/src/main/java/org/apache/hc/client5/http/impl/RequestSupport.java
+++ b/httpclient5/src/main/java/org/apache/hc/client5/http/impl/RequestSupport.java
@@ -113,7 +113,8 @@ public static String extractPathPrefix(final HttpRequest request) {
                         requiresOptimization = true;
                     }
                 }
-                if (ch == '.' || ch != '/' && !UNRESERVED.get(ch)) {
+                // Only a dot at the start of a segment can begin a dot segment
+                if (ch == '.' && previous == '/' || ch != '/' && !UNRESERVED.get(ch)) {
                     requiresOptimization = true;
                 }
                 previous = ch;
diff --git a/httpclient5/src/test/java/org/apache/hc/client5/http/impl/TestRequestSupport.java b/httpclient5/src/test/java/org/apache/hc/client5/http/impl/TestRequestSupport.java
index eb840fab77..e3912f4d87 100644
--- a/httpclient5/src/test/java/org/apache/hc/client5/http/impl/TestRequestSupport.java
+++ b/httpclient5/src/test/java/org/apache/hc/client5/http/impl/TestRequestSupport.java
@@ -55,4 +55,18 @@ void testPathPrefixExtraction() {
         Assertions.assertEquals("/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "")));
     }
 
+    @Test
+    void testPathPrefixExtractionDots() {
+        Assertions.assertEquals("/aaaa/b.b/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/b.b/cccc")));
+        Assertions.assertEquals("/aaaa/bbbb/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/bbbb/cc.cc")));
+        Assertions.assertEquals("/a.a/b..b/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/a.a/b..b/c.")));
+        Assertions.assertEquals("/aaaa/.bbbb/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/.bbbb/cccc")));
+        Assertions.assertEquals("/aaaa/.../", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/.../cccc")));
+        Assertions.assertEquals("/aaaa/bbbb/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/./bbbb/cccc")));
+        Assertions.assertEquals("/aaaa/bbbb/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/bbbb/.")));
+        Assertions.assertEquals("/cccc/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "/aaaa/%2E%2E/cccc/dddd")));
+        Assertions.assertEquals("/aaaa/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "../aaaa/bbbb")));
+        Assertions.assertEquals("/foo.bar/", RequestSupport.extractPathPrefix(new BasicHttpRequest("GET", "foo.bar/baz")));
+    }
+
 }