diff --git a/alire.toml b/alire.toml
index a2e72c926..d9ab5289d 100644
--- a/alire.toml
+++ b/alire.toml
@@ -69,7 +69,7 @@ commit = "56bbdc008e16996b6f76e443fd0165a240de1b13"
 
 [pins.den]
 url    = "https://github.com/mosteo/den"
-commit = "35d1f38395b93766dd64bca5901ce3b6a416ba1a"
+commit = "681ab5ca522585953f2e1d70763731df34c96012"
 
 [pins.dirty_booleans]
 url    = "https://github.com/mosteo/dirty_booleans"
diff --git a/deps/den b/deps/den
index 35d1f3839..681ab5ca5 160000
--- a/deps/den
+++ b/deps/den
@@ -1 +1 @@
-Subproject commit 35d1f38395b93766dd64bca5901ce3b6a416ba1a
+Subproject commit 681ab5ca522585953f2e1d70763731df34c96012
diff --git a/src/alire/alire-builds.adb b/src/alire/alire-builds.adb
index 9593c1c77..373bcbff2 100644
--- a/src/alire/alire-builds.adb
+++ b/src/alire/alire-builds.adb
@@ -7,7 +7,7 @@ with Alire.Paths.Vault;
 with Alire.Roots;
 with Alire.Settings.Builtins;
 
-with GNATCOLL.VFS;
+with Den.Filesystem;
 
 package body Alire.Builds is
 
@@ -56,16 +56,14 @@ package body Alire.Builds is
                   Simple_Logging.Activity
                     ("Syncing " & Release.Milestone.TTY_Image)
                     with Unreferenced;
-         Success : Boolean := False;
-         use GNATCOLL.VFS;
       begin
-         GNATCOLL.VFS.Copy
-           (Create (+Src),
-            +Dst,
-            Success);
-
-         Assert (Success,
-                 "Could not sync build dir from " & Src & " to " & Dst);
+         Den.Filesystem.Create_Directory (Dst);
+         Den.Filesystem.Copy (Src, Dst);
+      exception
+         when E : others =>
+            Log_Exception (E);
+            Raise_Checked_Error
+              ("Could not sync build dir from " & Src & " to " & Dst);
       end;
 
       --  At this point we can generate the final crate configuration
diff --git a/testsuite/drivers/builds.py b/testsuite/drivers/builds.py
index 48ff323d9..05e6359c7 100644
--- a/testsuite/drivers/builds.py
+++ b/testsuite/drivers/builds.py
@@ -83,14 +83,9 @@ def sync() -> None:
     """
     Sync the shared build directory
     """
-    # We force the sync by running a build, no matter if it succeeds or not
-    try:
-        subprocess.run(["alr", "-q", "-d", "build"]
-                       , stdout=subprocess.DEVNULL
-                       , stderr=subprocess.DEVNULL
-                       )
-    except:
-        pass
+    run_alr("build", "--stop-after=generation")
+    return
+
 
 def sync_builds() -> None:
     sync()
diff --git a/testsuite/tests/cache/softlinks/my_index/crate-0.1.0.tgz b/testsuite/tests/cache/softlinks/my_index/crate-0.1.0.tgz
new file mode 100644
index 000000000..4e90424e3
Binary files /dev/null and b/testsuite/tests/cache/softlinks/my_index/crate-0.1.0.tgz differ
diff --git a/testsuite/tests/cache/softlinks/my_index/index/cr/crate/crate-0.1.0.toml b/testsuite/tests/cache/softlinks/my_index/index/cr/crate/crate-0.1.0.toml
new file mode 100644
index 000000000..a4b05f347
--- /dev/null
+++ b/testsuite/tests/cache/softlinks/my_index/index/cr/crate/crate-0.1.0.toml
@@ -0,0 +1,11 @@
+description = "Example crate"
+name = "crate"
+version = "0.1.0"
+licenses = "GPL-3.0-only"
+maintainers = ["example@example.com"]
+maintainers-logins = ["mylogin"]
+executables=['main']
+
+[origin]
+url = "file:../../../crate-0.1.0.tgz"
+hashes = ["sha256:e246305107429e936610677bf5244d69510341a7df47cfce9e2278c4ad7da947"]
diff --git a/testsuite/tests/cache/softlinks/my_index/index/index.toml b/testsuite/tests/cache/softlinks/my_index/index/index.toml
new file mode 100644
index 000000000..bad265e4f
--- /dev/null
+++ b/testsuite/tests/cache/softlinks/my_index/index/index.toml
@@ -0,0 +1 @@
+version = "1.1"
diff --git a/testsuite/tests/cache/softlinks/test.py b/testsuite/tests/cache/softlinks/test.py
new file mode 100644
index 000000000..fd74e9e1f
--- /dev/null
+++ b/testsuite/tests/cache/softlinks/test.py
@@ -0,0 +1,60 @@
+"""
+Test proper syncing of softlinks, even bad ones
+
+This test is Unix-only, as Windows' tar cannot recreate the broken links:
+
+crate-0.1.0
+└── crate
+    ├── bin -> subdir/bin
+    ├── broken -> missing
+    ├── lib
+    │   ├── mock.so -> mock.so.0.0
+    │   ├── mock.so.0 -> mock.so.0.0
+    │   ├── mock.so.0.0
+    │   ├── zzz.so -> mock.so
+    │   └── zzz.so.0 -> mock.so
+    ├── loop
+    │   ├── x -> z
+    │   ├── y -> x
+    │   └── z -> y
+    ├── order
+    │   ├── ab -> b
+    │   ├── af -> d/f
+    │   ├── b
+    │   ├── cb -> b
+    │   ├── d
+    │   │   └── f
+    │   └── zf -> d/f
+    ├── self -> self
+    ├── subdir
+    │   ├── bin
+    │   │   ├── loop -> ../../subdir
+    │   │   └── x
+    │   ├── parent -> ..
+    │   └── self -> ../subdir
+    ├── that -> this
+    └── this -> that
+
+"""
+
+import os
+import shutil
+import drivers.builds as builds
+from drivers.alr import alr_with, init_local_crate, run_alr
+
+
+init_local_crate()
+
+# Make the crate depend on our troublesome crate and ensure syncing
+alr_with("crate")
+builds.sync()
+
+# Ensure that a copy has been made to the cache
+if builds.are_shared():
+    assert os.path.exists(builds.find_dir("crate"))
+
+# Cleanup
+os.chdir("..")
+shutil.rmtree("xxx")
+
+print('SUCCESS')
diff --git a/testsuite/tests/cache/softlinks/test.yaml b/testsuite/tests/cache/softlinks/test.yaml
new file mode 100644
index 000000000..f0325a232
--- /dev/null
+++ b/testsuite/tests/cache/softlinks/test.yaml
@@ -0,0 +1,8 @@
+driver: python-script
+build_mode: both
+control:
+    - [SKIP, "skip_unix",    "Test is Unix-only"]
+indexes:
+    my_index:
+        in_fixtures: false
+    compiler_only_index: {}