diff --git a/include/git2/diff.h b/include/git2/diff.h
index 9fcc3bb08..cac3b268a 100644
--- a/include/git2/diff.h
+++ b/include/git2/diff.h
@@ -124,6 +124,11 @@ typedef enum {
 	/** Use case insensitive filename comparisons */
 	GIT_DIFF_IGNORE_CASE = (1u << 10),
 
+	/** May be combined with `GIT_DIFF_IGNORE_CASE` to specify that a file
+	 *  that has changed case will be returned as an add/delete pair.
+	 */
+	GIT_DIFF_INCLUDE_CASECHANGE = (1u << 11),
+
 	/** If the pathspec is set in the diff options, this flags means to
 	 *  apply it as an exact match instead of as an fnmatch pattern.
 	 */
@@ -220,7 +225,7 @@ typedef struct git_diff git_diff;
 typedef enum {
 	GIT_DIFF_FLAG_BINARY     = (1u << 0), /**< file(s) treated as binary data */
 	GIT_DIFF_FLAG_NOT_BINARY = (1u << 1), /**< file(s) treated as text data */
-	GIT_DIFF_FLAG_VALID_ID  = (1u << 2), /**< `id` value is known correct */
+	GIT_DIFF_FLAG_VALID_ID   = (1u << 2), /**< `id` value is known correct */
 } git_diff_flag_t;
 
 /**
diff --git a/src/checkout.c b/src/checkout.c
index dd10732b5..a647ce0b9 100644
--- a/src/checkout.c
+++ b/src/checkout.c
@@ -2485,7 +2485,8 @@ int git_checkout_iterator(
 		GIT_DIFF_INCLUDE_IGNORED |
 		GIT_DIFF_INCLUDE_TYPECHANGE |
 		GIT_DIFF_INCLUDE_TYPECHANGE_TREES |
-		GIT_DIFF_SKIP_BINARY_CHECK;
+		GIT_DIFF_SKIP_BINARY_CHECK |
+		GIT_DIFF_INCLUDE_CASECHANGE;
 	if (data.opts.checkout_strategy & GIT_CHECKOUT_DISABLE_PATHSPEC_MATCH)
 		diff_opts.flags |= GIT_DIFF_DISABLE_PATHSPEC_MATCH;
 	if (data.opts.paths.count > 0)
diff --git a/src/diff.c b/src/diff.c
index 08e218cce..f7e1c8ee4 100644
--- a/src/diff.c
+++ b/src/diff.c
@@ -822,6 +822,19 @@ static int maybe_modified(
 			status = GIT_DELTA_UNMODIFIED;
 	}
 
+	/* If we want case changes, then break this into a delete of the old
+	 * and an add of the new so that consumers can act accordingly (eg,
+	 * checkout will update the case on disk.)
+	 */
+	if (DIFF_FLAG_IS_SET(diff, GIT_DIFF_IGNORE_CASE) &&
+		DIFF_FLAG_IS_SET(diff, GIT_DIFF_INCLUDE_CASECHANGE) &&
+		strcmp(oitem->path, nitem->path) != 0) {
+
+		if (!(error = diff_delta__from_one(diff, GIT_DELTA_DELETED, oitem)))
+			error = diff_delta__from_one(diff, GIT_DELTA_ADDED, nitem);
+		return error;
+	}
+
 	return diff_delta__from_two(
 		diff, status, oitem, omode, nitem, nmode,
 		git_oid_iszero(&noid) ? NULL : &noid, matched_pathspec);