diff --git a/src/core/parse.c b/src/core/parse.c
index 6faa7948a..c9177316f 100644
--- a/src/core/parse.c
+++ b/src/core/parse.c
@@ -363,8 +363,7 @@ static int stringend(JanetParser *p, JanetParseState *state) {
         JanetParseState top = p->states[p->statecount - 1];
         int32_t indent_col = (int32_t) top.column - 1;
         uint8_t *r = bufstart, *end = r + buflen;
-        /* Check if there are any characters before the start column -
-         * if so, do not reindent. */
+        /* Unless there are only spaces before EOLs, disable reindenting */
         int reindent = 1;
         while (reindent && (r < end)) {
             if (*r++ == '\n') {
@@ -374,34 +373,36 @@ static int stringend(JanetParser *p, JanetParseState *state) {
                         break;
                     }
                 }
+                if ((r + 1) < end && *r == '\r' && *(r + 1) == '\n') reindent = 1;
             }
         }
-        /* Now reindent if able to, otherwise just drop leading newline. */
-        if (!reindent) {
-            if (buflen > 0 && bufstart[0] == '\n') {
-                buflen--;
-                bufstart++;
-            }
-        } else {
+        /* Now reindent if able */
+        if (reindent) {
             uint8_t *w = bufstart;
             r = bufstart;
             while (r < end) {
                 if (*r == '\n') {
-                    if (r == bufstart) {
-                        /* Skip leading newline */
-                        r++;
-                    } else {
-                        *w++ = *r++;
-                    }
+                    *w++ = *r++;
                     for (int32_t j = 0; (r < end) && (*r != '\n') && (j < indent_col); j++, r++);
+                    if ((r + 1) < end && *r == '\r' && *(r + 1) == '\n') *w++ = *r++;
                 } else {
                     *w++ = *r++;
                 }
             }
             buflen = (int32_t)(w - bufstart);
         }
-        /* Check for trailing newline character so we can remove it */
-        if (buflen > 0 && bufstart[buflen - 1] == '\n') {
+        /* Check for leading EOL so we can remove it */
+        if (buflen > 1 && bufstart[0] == '\r' && bufstart[1] == '\n') { /* Windows EOL */
+            buflen = buflen - 2;
+            bufstart = bufstart + 2;
+        } else if (buflen > 0 && bufstart[0] == '\n') { /* Unix EOL */
+            buflen--;
+            bufstart++;
+        }
+        /* Check for trailing EOL so we can remove it */
+        if (buflen > 1 && bufstart[buflen - 2] == '\r' && bufstart[buflen - 1] == '\n') { /* Windows EOL */
+            buflen = buflen - 2;
+        } else if (buflen > 0 && bufstart[buflen - 1] == '\n') { /* Unix EOL */
             buflen--;
         }
     }
diff --git a/test/suite-parse.janet b/test/suite-parse.janet
index 941541204..05b34292c 100644
--- a/test/suite-parse.janet
+++ b/test/suite-parse.janet
@@ -57,6 +57,8 @@
     (for i (+ index 1) (+ index indent 1)
       (case (get text i)
         nil (break)
+        (chr "\r") (if-not (= (chr "\n") (get text (inc i)))
+                     (set rewrite false))
         (chr "\n") (break)
         (chr " ") nil
         (set rewrite false))))
@@ -64,12 +66,17 @@
   # Only re-indent if no dedented characters.
   (def str
     (if rewrite
-      (peg/replace-all ~(* "\n" (between 0 ,indent " ")) "\n" text)
+      (peg/replace-all ~(* '(* (? "\r") "\n") (between 0 ,indent " "))
+                      (fn [mtch eol] eol) text)
       text))
 
-  (def first-nl (= (chr "\n") (first str)))
-  (def last-nl (= (chr "\n") (last str)))
-  (string/slice str (if first-nl 1 0) (if last-nl -2)))
+  (def first-eol (cond
+                   (string/has-prefix? "\r\n" str) :crlf
+                   (string/has-prefix? "\n" str) :lf))
+  (def last-eol (cond
+                  (string/has-suffix? "\r\n" str) :crlf
+                  (string/has-suffix? "\n" str) :lf))
+  (string/slice str (case first-eol :crlf 2 :lf 1 0) (case last-eol :crlf -3 :lf -2)))
 
 (defn reindent-reference
   "Same as reindent but use parser functionality. Useful for
@@ -89,8 +96,10 @@
   (let [a (reindent text indent)
         b (reindent-reference text indent)]
     (assert (= a b)
-            (string "indent " indent-counter " (indent=" indent ")"))))
+            (string/format "reindent: %q, parse: %q (indent-test #%d with indent of %d)" a b indent-counter indent)
+            )))
 
+# Unix EOLs
 (check-indent "" 0)
 (check-indent "\n" 0)
 (check-indent "\n" 1)
@@ -106,6 +115,17 @@
 (check-indent "\n    Hello, world!\n    " 4)
 (check-indent "\n    Hello, world!\n   dedented text\n    " 4)
 (check-indent "\n    Hello, world!\n    indented text\n    " 4)
+# Windows EOLs
+(check-indent "\r\n" 0)
+(check-indent "\r\n" 1)
+(check-indent "\r\n\r\n" 0)
+(check-indent "\r\n\r\n" 1)
+(check-indent "\r\nHello, world!" 0)
+(check-indent "\r\nHello, world!" 1)
+(check-indent "\r\n    Hello, world!\r\n   " 4)
+(check-indent "\r\n    Hello, world!\r\n    " 4)
+(check-indent "\r\n    Hello, world!\r\n   dedented text\r\n    " 4)
+(check-indent "\r\n    Hello, world!\r\n    indented text\r\n    " 4)
 
 # Symbols with @ character
 # d68eae9