diff --git a/httpcore5/src/main/java/org/apache/hc/core5/net/URIBuilder.java b/httpcore5/src/main/java/org/apache/hc/core5/net/URIBuilder.java
index f5ca7afaa..218f300a5 100644
--- a/httpcore5/src/main/java/org/apache/hc/core5/net/URIBuilder.java
+++ b/httpcore5/src/main/java/org/apache/hc/core5/net/URIBuilder.java
@@ -1163,7 +1163,7 @@ static List<String> optimizePathSegments(final List<String> inputSegments) {
             }
             if (!inputSegments.isEmpty()) {
                 final String lastSegment = inputSegments.get(inputSegments.size() - 1);
-                if (lastSegment.isEmpty()) {
+                if (lastSegment.isEmpty() || lastSegment.equals("..") || lastSegment.equals(".")) {
                     outputSegments.addLast("");
                 }
             }
diff --git a/httpcore5/src/test/java/org/apache/hc/core5/net/TestURIBuilder.java b/httpcore5/src/test/java/org/apache/hc/core5/net/TestURIBuilder.java
index 42d0f00e2..fcef8d125 100644
--- a/httpcore5/src/test/java/org/apache/hc/core5/net/TestURIBuilder.java
+++ b/httpcore5/src/test/java/org/apache/hc/core5/net/TestURIBuilder.java
@@ -877,6 +877,12 @@ void testOptimize() throws Exception {
                 new URIBuilder("file:../../.././").optimize().build().toASCIIString());
         Assertions.assertEquals("http://host/",
                 new URIBuilder("http://host/../../.././").optimize().build().toASCIIString());
+        Assertions.assertEquals("http://host/a/",
+                new URIBuilder("http://host/a/b/..").optimize().build().toASCIIString());
+        Assertions.assertEquals("http://host/a/b/",
+                new URIBuilder("http://host/a/b/.").optimize().build().toASCIIString());
+        Assertions.assertEquals("http://host/a/b/..../...",
+                new URIBuilder("http://host/a/b/..../...").optimize().build().toASCIIString());
         Assertions.assertThrows(URISyntaxException.class, () -> new URIBuilder("http:///../../.././").optimize().build().toASCIIString());
     }