diff --git a/src/tool_operhlp.c b/src/tool_operhlp.c
index a0ae58f223..0277657526 100644
--- a/src/tool_operhlp.c
+++ b/src/tool_operhlp.c
@@ -198,19 +198,19 @@ CURLcode get_url_file_name(char **filename, const char *url, SANITIZEcode *sc)
     curl_url_cleanup(uh);
     uh = NULL;
     if(!uerr) {
-      int i;
       char *pc = NULL, *pc2 = NULL;
-      for(i = 0; i < 2; i++) {
+      do {
         pc = strrchr(path, '/');
         pc2 = strrchr(pc ? pc + 1 : path, '\\');
         if(pc2)
           pc = pc2;
-        if(pc && !pc[1] && !i) {
+        if(pc && !pc[1])
           /* if the path ends with slash, try removing the trailing one
              and get the last directory part */
           *pc = 0;
-        }
-      }
+        else
+          break;
+      } while(1);
 
       if(pc) {
         /* duplicate the string beyond the slash */
diff --git a/tests/data/Makefile.am b/tests/data/Makefile.am
index 44473ecfa3..c080c32133 100644
--- a/tests/data/Makefile.am
+++ b/tests/data/Makefile.am
@@ -217,8 +217,7 @@ test1614 test1615 test1616 test1617 test1618 test1619 test1620 test1621 \
 test1622 test1623 test1624 test1625 test1626 test1627 \
 \
 test1630 test1631 test1632 test1633 test1634 test1635 test1636 test1637 \
-test1638 \
-test1640 test1641 test1642 test1643 \
+test1638 test1639 test1640 test1641 test1642 test1643 test1644 \
 \
 test1650 test1651 test1652 test1653 test1654 test1655 test1656 test1657 \
 test1658 test1659 test1660 test1661 test1662 test1663 test1664 test1665 \
diff --git a/tests/data/test1639 b/tests/data/test1639
new file mode 100644
index 0000000000..d171c3dc23
--- /dev/null
+++ b/tests/data/test1639
@@ -0,0 +1,65 @@
+<?xml version="1.0" encoding="US-ASCII"?>
+<testcase>
+<info>
+<keywords>
+HTTP
+HTTP GET
+</keywords>
+</info>
+
+# Server-side
+<reply>
+<data crlf="headers" nocheck="yes">
+HTTP/1.1 200 OK
+Date: Tue, 09 Nov 2010 14:49:00 GMT
+Server: test-server/fake
+Last-Modified: Tue, 13 Jun 2000 12:10:00 GMT
+ETag: "21025-dc7-39462498"
+Accept-Ranges: bytes
+Content-Length: 6
+Connection: close
+Content-Type: text/html
+Funny-head: yesyes
+
+-foo-
+</data>
+</reply>
+
+# Client-side
+<client>
+<server>
+http
+</server>
+<name>
+-O with URL without path using many trailing slashes
+</name>
+<command option="no-output">
+http://%HOSTIP:%HTTPPORT///////////////// -O --output-dir %LOGDIR
+</command>
+</client>
+
+# Verify data after the test has been "shot"
+<verify>
+<protocol crlf="headers">
+GET ///////////////// HTTP/1.1
+Host: %HOSTIP:%HTTPPORT
+User-Agent: curl/%VERSION
+Accept: */*
+
+</protocol>
+<file name="%LOGDIR/curl_response" crlf="headers">
+HTTP/1.1 200 OK
+Date: Tue, 09 Nov 2010 14:49:00 GMT
+Server: test-server/fake
+Last-Modified: Tue, 13 Jun 2000 12:10:00 GMT
+ETag: "21025-dc7-39462498"
+Accept-Ranges: bytes
+Content-Length: 6
+Connection: close
+Content-Type: text/html
+Funny-head: yesyes
+
+-foo-
+</file>
+</verify>
+</testcase>
diff --git a/tests/data/test1644 b/tests/data/test1644
new file mode 100644
index 0000000000..14cd7cec7f
--- /dev/null
+++ b/tests/data/test1644
@@ -0,0 +1,65 @@
+<?xml version="1.0" encoding="US-ASCII"?>
+<testcase>
+<info>
+<keywords>
+HTTP
+HTTP GET
+</keywords>
+</info>
+
+# Server-side
+<reply>
+<data crlf="headers" nocheck="yes">
+HTTP/1.1 200 OK
+Date: Tue, 09 Nov 2010 14:49:00 GMT
+Server: test-server/fake
+Last-Modified: Tue, 13 Jun 2000 12:10:00 GMT
+ETag: "21025-dc7-39462498"
+Accept-Ranges: bytes
+Content-Length: 6
+Connection: close
+Content-Type: text/html
+Funny-head: yesyes
+
+-foo-
+</data>
+</reply>
+
+# Client-side
+<client>
+<server>
+http
+</server>
+<name>
+-O with URL with path but using many trailing slashes
+</name>
+<command option="no-output">
+http://%HOSTIP:%HTTPPORT///foo////////////// -O --output-dir %LOGDIR
+</command>
+</client>
+
+# Verify data after the test has been "shot"
+<verify>
+<protocol crlf="headers">
+GET ///foo////////////// HTTP/1.1
+Host: %HOSTIP:%HTTPPORT
+User-Agent: curl/%VERSION
+Accept: */*
+
+</protocol>
+<file name="%LOGDIR/foo" crlf="headers">
+HTTP/1.1 200 OK
+Date: Tue, 09 Nov 2010 14:49:00 GMT
+Server: test-server/fake
+Last-Modified: Tue, 13 Jun 2000 12:10:00 GMT
+ETag: "21025-dc7-39462498"
+Accept-Ranges: bytes
+Content-Length: 6
+Connection: close
+Content-Type: text/html
+Funny-head: yesyes
+
+-foo-
+</file>
+</verify>
+</testcase>