diff --git a/tools/upip.py b/tools/upip.py
index a156340b20..7b85c718f2 100644
--- a/tools/upip.py
+++ b/tools/upip.py
@@ -104,6 +104,10 @@ import usocket
 warn_ussl = True
 def url_open(url):
     global warn_ussl
+
+    if debug:
+        print(url)
+
     proto, _, host, urlpath = url.split('/', 3)
     try:
         ai = usocket.getaddrinfo(host, 443)
@@ -113,41 +117,43 @@ def url_open(url):
     addr = ai[0][4]
 
     s = usocket.socket(ai[0][0])
-    #print("Connect address:", addr)
-    s.connect(addr)
+    try:
+        #print("Connect address:", addr)
+        s.connect(addr)
 
-    if proto == "https:":
-        s = ussl.wrap_socket(s)
-        if warn_ussl:
-            print("Warning: %s SSL certificate is not validated" % host)
-            warn_ussl = False
+        if proto == "https:":
+            s = ussl.wrap_socket(s)
+            if warn_ussl:
+                print("Warning: %s SSL certificate is not validated" % host)
+                warn_ussl = False
 
-    # MicroPython rawsocket module supports file interface directly
-    s.write("GET /%s HTTP/1.0\r\nHost: %s\r\n\r\n" % (urlpath, host))
-    l = s.readline()
-    protover, status, msg = l.split(None, 2)
-    if status != b"200":
-        s.close()
-        exc = ValueError(status)
-        if status == b"404":
-            fatal("Package not found", exc)
-        fatal("Unexpected error querying for package", exc)
-    while 1:
+        # MicroPython rawsocket module supports file interface directly
+        s.write("GET /%s HTTP/1.0\r\nHost: %s\r\n\r\n" % (urlpath, host))
         l = s.readline()
-        if not l:
-            s.close()
-            fatal("Unexpected EOF in HTTP headers", ValueError())
-        if l == b'\r\n':
-            break
+        protover, status, msg = l.split(None, 2)
+        if status != b"200":
+            if status == b"404" or status == b"301":
+                raise NotFoundError("Package not found")
+            raise ValueError(status)
+        while 1:
+            l = s.readline()
+            if not l:
+                raise ValueError("Unexpected EOF in HTTP headers")
+            if l == b'\r\n':
+                break
+    except Exception as e:
+        s.close()
+        raise e
 
     return s
 
 
 def get_pkg_metadata(name):
     f = url_open("https://pypi.python.org/pypi/%s/json" % name)
-    s = f.read()
-    f.close()
-    return json.loads(s)
+    try:
+        return json.load(f)
+    finally:
+        f.close()
 
 
 def fatal(msg, exc=None):
@@ -168,10 +174,12 @@ def install_pkg(pkg_spec, install_path):
     print("Installing %s %s from %s" % (pkg_spec, latest_ver, package_url))
     package_fname = op_basename(package_url)
     f1 = url_open(package_url)
-    f2 = uzlib.DecompIO(f1, gzdict_sz)
-    f3 = tarfile.TarFile(fileobj=f2)
-    meta = install_tar(f3, install_path)
-    f1.close()
+    try:
+        f2 = uzlib.DecompIO(f1, gzdict_sz)
+        f3 = tarfile.TarFile(fileobj=f2)
+        meta = install_tar(f3, install_path)
+    finally:
+        f1.close()
     del f3
     del f2
     gc.collect()
@@ -208,9 +216,10 @@ def install(to_install, install_path=None):
             if deps:
                 deps = deps.decode("utf-8").split("\n")
                 to_install.extend(deps)
-    except NotFoundError:
-        print("Error: cannot find '%s' package (or server error), packages may be partially installed" \
-            % pkg_spec, file=sys.stderr)
+    except Exception as e:
+        print("Error installing '{}': {}, packages may be partially installed".format(
+                pkg_spec, e),
+            file=sys.stderr)
 
 def get_install_path():
     global install_path