diff --git a/cf-agent/simulate_mode.c b/cf-agent/simulate_mode.c
index b70274a9c13..bf5343bd449 100644
--- a/cf-agent/simulate_mode.c
+++ b/cf-agent/simulate_mode.c
@@ -827,7 +827,10 @@ bool DiffPkgOperations()
             MapRemove(removed, name_arch);
 
             PkgOperationRecord *prev_record = MapGet(installed, name_arch);
-            if ((prev_record == NULL) || PkgVersionIsGreater(pkg_ver, prev_record->pkg_ver))
+            if ((prev_record == NULL) ||
+                (NULL_OR_EMPTY(prev_record->pkg_ver) && !NULL_OR_EMPTY(pkg_ver)) ||
+                (!NULL_OR_EMPTY(pkg_ver) && !NULL_OR_EMPTY(prev_record->pkg_ver) &&
+                 PkgVersionIsGreater(pkg_ver, prev_record->pkg_ver)))
             {
                 char *msg = GetPkgOperationMsg(CHROOT_PKG_OPERATION_CODE_INSTALL,
                                                pkg_name, pkg_arch, pkg_ver);
diff --git a/tests/unit/simulate_mode_test.c b/tests/unit/simulate_mode_test.c
index 10b5513121a..87d71b4cc63 100644
--- a/tests/unit/simulate_mode_test.c
+++ b/tests/unit/simulate_mode_test.c
@@ -147,6 +147,40 @@ static void test_manifest_install_cancels_removal(void)
     unlink(ToChangesChroot(CHROOT_PKGS_OPS_FILE));
 }
 
+/* Two recorded installations of the same package without a version must be
+ * reported once, not abort on comparing the empty versions. */
+static void test_diff_repeated_unversioned_install(void)
+{
+    write_pkgs_ops("i,foo,,\r\n"
+                   "i,foo,,\r\n");
+
+    char output[4096];
+    assert_true(call_with_captured_stdout(&DiffPkgOperations, output, sizeof(output)));
+
+    const char *msg = "Package 'foo' would be installed";
+    const char *first = strstr(output, msg);
+    assert_true(first != NULL);
+    assert_true(strstr(first + strlen(msg), "would be installed") == NULL);
+
+    unlink(ToChangesChroot(CHROOT_PKGS_OPS_FILE));
+}
+
+/* A versioned installation record is more specific than an unversioned one
+ * of the same package, so it is the one to report. */
+static void test_diff_unversioned_then_versioned_install(void)
+{
+    write_pkgs_ops("i,foo,,\r\n"
+                   "i,foo,1.2.3,\r\n");
+
+    char output[4096];
+    assert_true(call_with_captured_stdout(&DiffPkgOperations, output, sizeof(output)));
+
+    assert_true(strstr(output, "Package 'foo [1.2.3]' would be installed") != NULL);
+    assert_true(strstr(output, "Package 'foo' would be installed") == NULL);
+
+    unlink(ToChangesChroot(CHROOT_PKGS_OPS_FILE));
+}
+
 int main()
 {
     PRINT_TEST_BANNER();
@@ -161,6 +195,8 @@ int main()
         unit_test(test_diff_removal_with_version),
         unit_test(test_diff_removal_with_other_version_keeps_install),
         unit_test(test_manifest_install_cancels_removal),
+        unit_test(test_diff_repeated_unversioned_install),
+        unit_test(test_diff_unversioned_then_versioned_install),
     };
 
     int ret = run_tests(tests);