diff --git a/bootstrap.sh b/bootstrap.sh
index fbf577e62..00dba3eb2 100755
--- a/bootstrap.sh
+++ b/bootstrap.sh
@@ -17,7 +17,8 @@ if [ $? -ne 0 ]; then
     exit 1
 fi
 cd "$pwd"
-cp "./src/engine/b2" .
+cp "./src/engine/b2" . 2>/dev/null
+cp "./src/engine/b2.exe" . 2>/dev/null
 
 cat << EOF
 
diff --git a/src/tools/link.jam b/src/tools/link.jam
index e9e8851fe..fa4070e34 100644
--- a/src/tools/link.jam
+++ b/src/tools/link.jam
@@ -229,8 +229,8 @@ class symlink-target-class : basic-target
 
 rule do-file-link
 {
-    local target = [ path.native [ path.relative-to [ path.pwd ] $(<) ] ] ;
-    local source = [ path.native [ path.relative-to [ path.pwd ] $(>) ] ] ;
+    local target = [ path.relative-to [ path.pwd ] $(<) ] ;
+    local source = [ path.relative-to [ path.pwd ] $(>) ] ;
     local old-source = [ on $(target) return $(LINK-SOURCE) ] ;
     if $(old-source)
     {
@@ -240,6 +240,8 @@ rule do-file-link
             Link previously defined to another file, $(old-source[1]). ;
     }
     LINK-SOURCE on $(target) = $(source) $(.current-target) ;
+    target = [ path.native $(target) ] ;
+    source = [ path.native $(source) ] ;
     LOCATE on $(target) = . ;
     DEPENDS $(.current-target) : $(target) ;
     if $(.can-symlink) = true
diff --git a/test/BoostBuild.py b/test/BoostBuild.py
index 786ec392b..ff205f5b1 100644
--- a/test/BoostBuild.py
+++ b/test/BoostBuild.py
@@ -112,12 +112,9 @@ def get_toolset():
 
 
 # Detect the host OS.
-cygwin = hasattr(os, "uname") and os.uname()[0].lower().startswith("cygwin")
-windows = cygwin or os.environ.get("OS", "").lower().startswith("windows")
-
-if cygwin:
+if sys.platform == "cygwin":
     default_os = "cygwin"
-elif windows:
+elif sys.platform == "win32":
     default_os = "windows"
 elif hasattr(os, "uname"):
     default_os = os.uname()[0].lower()
@@ -158,7 +155,7 @@ def prepare_suffix_map(toolset, target_os=default_os):
     if target_os == "cygwin":
         suffixes[".lib"] = ".a"
         suffixes[".obj"] = ".o"
-        suffixes[".implib"] = ".lib.a"
+        suffixes[".implib"] = ".dll.a"
     elif target_os == "windows":
         if toolset == "gcc":
             # MinGW
@@ -196,6 +193,11 @@ def prepare_library_prefix(toolset, target_os=default_os):
     else:
         dll_prefix = "lib"
 
+    global implib_prefix
+    implib_prefix = None
+    if toolset == "gcc":
+        implib_prefix = "lib"
+
 
 def re_remove(sequence, regex):
     me = re.compile(regex)
@@ -268,7 +270,7 @@ class Tester(TestCmd.TestCmd):
         if not executable:
             executable = os.getenv('B2')
         if not executable:
-            executable = 'b2' if os.name != 'nt' else 'b2.exe'
+            executable = 'b2' if sys.platform not in ['win32', 'cygwin'] else 'b2.exe'
 
         assert arguments.__class__ is not str
         self.original_workdir = os.path.dirname(__file__)
@@ -280,6 +282,7 @@ class Tester(TestCmd.TestCmd):
         self.translate_suffixes = translate_suffixes
         self.use_test_config = use_test_config
 
+        self.target_os = default_os
         self.toolset = get_toolset()
         self.expanded_toolset = expand_toolset(self.toolset)
         self.pass_toolset = pass_toolset
@@ -341,11 +344,14 @@ class Tester(TestCmd.TestCmd):
             pass
 
     def set_toolset(self, toolset, target_os=default_os):
+        self.target_os = target_os
         self.toolset = toolset
         self.expanded_toolset = expand_toolset(toolset, target_os)
         self.pass_toolset = True
         prepare_prefixes_and_suffixes(toolset, target_os)
 
+    def is_implib_expected(self):
+        return self.target_os in ["windows", "cygwin"] and not self.toolset.startswith("clang-linux")
 
     #
     # Methods that change the working directory's content.
@@ -741,7 +747,7 @@ class Tester(TestCmd.TestCmd):
     def __ignore_junk(self):
         # Not totally sure about this change, but I do not see a good
         # alternative.
-        if windows:
+        if self.target_os == "windows":
             self.ignore("*.ilk")       # MSVC incremental linking files.
             self.ignore("*.pdb")       # MSVC program database files.
             self.ignore("*.rsp")       # Response files.
@@ -838,21 +844,21 @@ class Tester(TestCmd.TestCmd):
     def adjust_lib_name(self, name):
         global lib_prefix
         global dll_prefix
+        global implib_prefix
         result = name
 
         pos = name.rfind(".")
         if pos != -1:
             suffix = name[pos:]
-            if suffix == ".lib":
-                (head, tail) = os.path.split(name)
-                if lib_prefix:
-                    tail = lib_prefix + tail
-                    result = os.path.join(head, tail)
-            elif suffix == ".dll" or suffix == ".implib":
-                (head, tail) = os.path.split(name)
-                if dll_prefix:
-                    tail = dll_prefix + tail
-                    result = os.path.join(head, tail)
+            prefix = {
+                 ".lib": lib_prefix,
+                 ".dll": dll_prefix,
+                 ".implib": implib_prefix,
+            }.get(suffix)
+            (head, tail) = os.path.split(name)
+            if prefix:
+                tail = prefix + tail
+                result = os.path.join(head, tail)
         # If we want to use this name in a Jamfile, we better convert \ to /,
         # as otherwise we would have to quote \.
         result = result.replace("\\", "/")
diff --git a/test/TestToolset.py b/test/TestToolset.py
index a1d5167ef..4ae3b2af9 100644
--- a/test/TestToolset.py
+++ b/test/TestToolset.py
@@ -119,7 +119,7 @@ def test_toolset(toolset, version, property_sets):
         t.run_build_system(["--user-config=", "-sPYTHON_CMD=%s" % sys.executable] + properties)
         t.expect_addition("bin/%s/lib.obj" % (path("obj")))
         if "link=static" not in properties:
-            if get_target_os(properties) in ["cygwin", "windows"] and toolset != "clang-linux":
+            if t.is_implib_expected():
                 t.expect_addition("bin/%s/l1.implib" % (path("dll")))
             t.expect_addition("bin/%s/l1.dll" % (path("dll")))
             t.ignore_addition("bin/%s/*l1.*.rsp" % (path("dll")))
diff --git a/test/builtin_readlink.py b/test/builtin_readlink.py
index ea6dadf9a..a76c9a5c2 100755
--- a/test/builtin_readlink.py
+++ b/test/builtin_readlink.py
@@ -7,12 +7,14 @@
 import BoostBuild
 import os
 import sys
+from unittest.mock import patch
 
 t = BoostBuild.Tester(pass_toolset=0)
 
 t.write("link-target", "")
 try:
-    os.symlink("link-target", "link")
+    with patch.dict(os.environ, {var: "winsymlinks:nativestrict" for var in ["MSYS", "CYGWIN"]}):
+        os.symlink("link-target", "link")
 except (AttributeError, OSError) as e:
     # Either OS does not support symlinks or not enough privilege
     print("XFAIL: %s" % e)
diff --git a/test/library_chain.py b/test/library_chain.py
index f8d9dccb6..d4291c318 100644
--- a/test/library_chain.py
+++ b/test/library_chain.py
@@ -117,7 +117,7 @@ void a() {}
 t.run_build_system(subdir="a")
 t.expect_addition("a/dist/a.dll")
 
-if sys.platform == 'win32':
+if t.is_implib_expected():
     # This is a Windows import library.
     file = t.adjust_name("a.implib")
 else:
diff --git a/test/link.py b/test/link.py
index 70a3d05c7..b2cfd1837 100755
--- a/test/link.py
+++ b/test/link.py
@@ -8,6 +8,8 @@
 # common boost/ directory in the new git layout.
 
 import BoostBuild
+import os
+from unittest.mock import patch
 
 def ignore_config(t):
     """These files are created by the configuration logic in link.jam
@@ -339,12 +341,14 @@ def test_error_duplicate():
 
     t.cleanup()
 
-test_basic()
-test_merge_two()
-test_merge_existing_all()
-test_merge_recursive()
-test_merge_recursive_existing_all()
-test_include_scan()
-test_include_scan_merge_existing()
-test_update_file_link_all()
-test_error_duplicate()
+
+with patch.dict(os.environ, {var: "winsymlinks:nativestrict" for var in ["MSYS", "CYGWIN"]}):
+    test_basic()
+    test_merge_two()
+    test_merge_existing_all()
+    test_merge_recursive()
+    test_merge_recursive_existing_all()
+    test_include_scan()
+    test_include_scan_merge_existing()
+    test_update_file_link_all()
+    test_error_duplicate()
diff --git a/test/prebuilt/ext/jamfile2.jam b/test/prebuilt/ext/jamfile2.jam
index 6481808c6..4c95a78d7 100644
--- a/test/prebuilt/ext/jamfile2.jam
+++ b/test/prebuilt/ext/jamfile2.jam
@@ -18,7 +18,7 @@ if [ os.name ] in NT
 }
 else if [ os.name ] in CYGWIN
 {
-    dll-suffix = dll ;
+    dll-suffix = dll.a ;
 }
 else if [ os.name ] in MACOSX
 {
diff --git a/test/prebuilt/ext/jamfile3.jam b/test/prebuilt/ext/jamfile3.jam
index be2257fa2..f90fc4486 100644
--- a/test/prebuilt/ext/jamfile3.jam
+++ b/test/prebuilt/ext/jamfile3.jam
@@ -22,7 +22,7 @@ if [ os.name ] in NT
 }
 else if [ os.name ] in CYGWIN
 {
-    dll-suffix = dll ;
+    dll-suffix = dll.a ;
 }
 else if [ os.name ] in MACOSX
 {
diff --git a/test/searched_lib.py b/test/searched_lib.py
index 6b84964d8..dee2b7298 100644
--- a/test/searched_lib.py
+++ b/test/searched_lib.py
@@ -31,8 +31,8 @@ t.expect_addition("lib/bin/$toolset/debug*/test_lib.dll")
 
 # Auto adjusting of suffixes does not work, since we need to
 # change dll to lib.
-if ( ( os.name == "nt" ) or os.uname()[0].lower().startswith("cygwin") ) and \
-    ( BoostBuild.get_toolset() != "gcc" ):
+if t.is_implib_expected():
+    t.expect_addition("lib/bin/$toolset/debug*/test_lib.implib")
     t.copy("lib/bin/$toolset/debug*/test_lib.implib", "lib/test_lib.implib")
     t.copy("lib/bin/$toolset/debug*/test_lib.dll", "lib/test_lib.dll")
 else: