diff --git a/src/builtins/test.cpp b/src/builtins/test.cpp
index 4f3d2f0ea..06c4b87a8 100644
--- a/src/builtins/test.cpp
+++ b/src/builtins/test.cpp
@@ -65,6 +65,10 @@ enum token_t {
     test_string_equal,      // "=", true if strings are identical
     test_string_not_equal,  // "!=", true if strings are not identical
 
+    test_file_newer, // f1 -nt f2, true if f1 exists and is newer than f2, or there is no f2
+    test_file_older, // f1 -ot f2, true if f2 exists and f1 does not, or f1 is older than f2
+    test_file_same,  // f1 -ef f2, true if f1 and f2 exist and refer to same file
+
     test_number_equal,          // "-eq", true if numbers are equal
     test_number_not_equal,      // "-ne", true if numbers are not equal
     test_number_greater,        // "-gt", true if first number is larger than second
@@ -152,6 +156,9 @@ static const token_info_t *token_for_string(const wcstring &str) {
         {L"-z", {test_string_z, UNARY_PRIMARY}},
         {L"=", {test_string_equal, BINARY_PRIMARY}},
         {L"!=", {test_string_not_equal, BINARY_PRIMARY}},
+        {L"-nt", {test_file_newer, BINARY_PRIMARY}},
+        {L"-ot", {test_file_older, BINARY_PRIMARY}},
+        {L"-ef", {test_file_same, BINARY_PRIMARY}},
         {L"-eq", {test_number_equal, BINARY_PRIMARY}},
         {L"-ne", {test_number_not_equal, BINARY_PRIMARY}},
         {L"-gt", {test_number_greater, BINARY_PRIMARY}},
@@ -742,6 +749,15 @@ static bool binary_primary_evaluate(test_expressions::token_t token, const wcstr
         case test_string_not_equal: {
             return left != right;
         }
+        case test_file_newer: {
+            return file_id_for_path(right).older_than(file_id_for_path(left));
+        }
+        case test_file_older: {
+            return file_id_for_path(left).older_than(file_id_for_path(right));
+        }
+        case test_file_same: {
+            return file_id_for_path(left) == file_id_for_path(right);
+        }
         case test_number_equal: {
             return parse_number(left, &ln, errors) && parse_number(right, &rn, errors) &&
                    ln.compare(rn) == 0;
diff --git a/src/wutil.cpp b/src/wutil.cpp
index 677e77cb3..ccfa05fbf 100644
--- a/src/wutil.cpp
+++ b/src/wutil.cpp
@@ -868,6 +868,22 @@ static int compare(T a, T b) {
     return 0;
 }
 
+/// \return true if \param rhs has higher mtime seconds than this file_id_t.
+/// If identical, nanoseconds are compared.
+bool file_id_t::older_than(const file_id_t &rhs) const {
+    int ret = compare(mod_seconds, rhs.mod_seconds);
+    if (!ret) ret = compare(mod_nanoseconds, rhs.mod_nanoseconds);
+    switch (ret) {
+        case -1:
+            return true;
+        case 1:
+        case 0:
+            return false;
+        default:
+            DIE("unreachable");
+    }
+}
+
 int file_id_t::compare_file_id(const file_id_t &rhs) const {
     // Compare each field, stopping when we get to a non-equal field.
     int ret = 0;
diff --git a/src/wutil.h b/src/wutil.h
index accb4e189..80e6c258c 100644
--- a/src/wutil.h
+++ b/src/wutil.h
@@ -145,9 +145,14 @@ struct file_id_t {
     dev_t device{static_cast<dev_t>(-1LL)};
     ino_t inode{static_cast<ino_t>(-1LL)};
     uint64_t size{static_cast<uint64_t>(-1LL)};
-    time_t change_seconds{-1};
+    /* some platforms handle negative time_t
+       values to represent WW1-era dates, initialize ancient
+       for the sake of comparisons.
+       tv_nsec's meaningful values are REALLY [0, 999999999]
+       this nanosecond component we'll initialize at 0. */
+    time_t change_seconds{std::numeric_limits<time_t>::min()};
     long change_nanoseconds{-1};
-    time_t mod_seconds{-1};
+    time_t mod_seconds{std::numeric_limits<time_t>::min()};
     long mod_nanoseconds{-1};
 
     constexpr file_id_t() = default;
@@ -159,7 +164,7 @@ struct file_id_t {
     bool operator<(const file_id_t &rhs) const;
 
     static file_id_t from_stat(const struct stat &buf);
-
+    bool older_than(const file_id_t &rhs) const;
     wcstring dump() const;
 
    private: