diff --git a/src/checkout.c b/src/checkout.c
index d5a471d0c..411bf3be7 100644
--- a/src/checkout.c
+++ b/src/checkout.c
@@ -224,7 +224,7 @@ static int checkout_action_wd_only(
 	if (!git_pathspec_match_path(
 			pathspec, wd->path,
 			(data->strategy & GIT_CHECKOUT_DISABLE_PATHSPEC_MATCH) != 0,
-			workdir->ignore_case))
+			git_iterator_ignore_case(workdir)))
 		return 0;
 
 	/* check if item is tracked in the index but not in the checkout diff */
@@ -1130,7 +1130,7 @@ static int checkout_data_init(
 		if ((error = git_config_refresh(cfg)) < 0)
 			goto cleanup;
 
-		if (git_iterator_inner_type(target) == GIT_ITERATOR_INDEX) {
+		if (git_iterator_inner_type(target) == GIT_ITERATOR_TYPE_INDEX) {
 			/* if we are iterating over the index, don't reload */
 			data->index = git_iterator_index_get_index(target);
 			GIT_REFCOUNT_INC(data->index);
@@ -1208,6 +1208,7 @@ int git_checkout_iterator(
 	git_diff_options diff_opts = GIT_DIFF_OPTIONS_INIT;
 	uint32_t *actions = NULL;
 	size_t *counts = NULL;
+	git_iterator_flag_t iterflags = 0;
 
 	/* initialize structures and options */
 	error = checkout_data_init(&data, target, opts);
@@ -1228,18 +1229,21 @@ int git_checkout_iterator(
 		diff_opts.pathspec = data.opts.paths;
 
 	/* set up iterators */
+
+	iterflags = git_iterator_ignore_case(target) ?
+		GIT_ITERATOR_IGNORE_CASE : GIT_ITERATOR_DONT_IGNORE_CASE;
+
 	if ((error = git_iterator_reset(target, data.pfx, data.pfx)) < 0 ||
 		(error = git_iterator_for_workdir_range(
-			&workdir, data.repo, data.pfx, data.pfx)) < 0 ||
+			&workdir, data.repo, iterflags, data.pfx, data.pfx)) < 0 ||
 		(error = git_iterator_for_tree_range(
-			&baseline, data.opts.baseline, data.pfx, data.pfx)) < 0)
+			&baseline, data.opts.baseline, iterflags, data.pfx, data.pfx)) < 0)
 		goto cleanup;
 
 	/* Handle case insensitivity for baseline if necessary */
-	if (workdir->ignore_case && !baseline->ignore_case) {
+	if (git_iterator_ignore_case(workdir) != git_iterator_ignore_case(baseline))
 		if ((error = git_iterator_spoolandsort_push(baseline, true)) < 0)
 			goto cleanup;
-	}
 
 	/* Generate baseline-to-target diff which will include an entry for
 	 * every possible update that might need to be made.
diff --git a/src/diff.c b/src/diff.c
index 5e34b9221..4b60935f0 100644
--- a/src/diff.c
+++ b/src/diff.c
@@ -418,7 +418,7 @@ static int maybe_modified(
 	git_delta_t status = GIT_DELTA_MODIFIED;
 	unsigned int omode = oitem->mode;
 	unsigned int nmode = nitem->mode;
-	bool new_is_workdir = (new_iter->type == GIT_ITERATOR_WORKDIR);
+	bool new_is_workdir = (new_iter->type == GIT_ITERATOR_TYPE_WORKDIR);
 
 	GIT_UNUSED(old_iter);
 
@@ -556,7 +556,9 @@ static int diff_list_init_from_iterators(
 
 	/* Use case-insensitive compare if either iterator has
 	 * the ignore_case bit set */
-	if (!old_iter->ignore_case && !new_iter->ignore_case) {
+	if (!git_iterator_ignore_case(old_iter) &&
+		!git_iterator_ignore_case(new_iter))
+	{
 		diff->opts.flags &= ~GIT_DIFF_DELTAS_ARE_ICASE;
 
 		diff->strcomp    = git__strcmp;
@@ -714,7 +716,7 @@ int git_diff__from_iterators(
 			else if (git_iterator_current_is_ignored(new_iter))
 				delta_type = GIT_DELTA_IGNORED;
 
-			else if (new_iter->type != GIT_ITERATOR_WORKDIR)
+			else if (new_iter->type != GIT_ITERATOR_TYPE_WORKDIR)
 				delta_type = GIT_DELTA_ADDED;
 
 			if (diff_delta__from_one(diff, delta_type, nitem) < 0)
@@ -786,8 +788,8 @@ int git_diff_tree_to_tree(
 	assert(diff && repo);
 
 	DIFF_FROM_ITERATORS(
-		git_iterator_for_tree_range(&a, old_tree, pfx, pfx),
-		git_iterator_for_tree_range(&b, new_tree, pfx, pfx)
+		git_iterator_for_tree_range(&a, old_tree, 0, pfx, pfx),
+		git_iterator_for_tree_range(&b, new_tree, 0, pfx, pfx)
 	);
 
 	return error;
@@ -808,8 +810,8 @@ int git_diff_tree_to_index(
 		return error;
 
 	DIFF_FROM_ITERATORS(
-		git_iterator_for_tree_range(&a, old_tree, pfx, pfx),
-	    git_iterator_for_index_range(&b, index, pfx, pfx)
+		git_iterator_for_tree_range(&a, old_tree, 0, pfx, pfx),
+	    git_iterator_for_index_range(&b, index, 0, pfx, pfx)
 	);
 
 	return error;
@@ -829,8 +831,8 @@ int git_diff_index_to_workdir(
 		return error;
 
 	DIFF_FROM_ITERATORS(
-		git_iterator_for_index_range(&a, index, pfx, pfx),
-	    git_iterator_for_workdir_range(&b, repo, pfx, pfx)
+		git_iterator_for_index_range(&a, index, 0, pfx, pfx),
+	    git_iterator_for_workdir_range(&b, repo, 0, pfx, pfx)
 	);
 
 	return error;
@@ -848,8 +850,8 @@ int git_diff_tree_to_workdir(
 	assert(diff && repo);
 
 	DIFF_FROM_ITERATORS(
-		git_iterator_for_tree_range(&a, old_tree, pfx, pfx),
-	    git_iterator_for_workdir_range(&b, repo, pfx, pfx)
+		git_iterator_for_tree_range(&a, old_tree, 0, pfx, pfx),
+	    git_iterator_for_workdir_range(&b, repo, 0, pfx, pfx)
 	);
 
 	return error;
diff --git a/src/diff_output.c b/src/diff_output.c
index d271e8a8e..8a7a7a2a1 100644
--- a/src/diff_output.c
+++ b/src/diff_output.c
@@ -495,7 +495,7 @@ static void diff_patch_init(
 		patch->old_src = patch->diff->old_src;
 		patch->new_src = patch->diff->new_src;
 	} else {
-		patch->old_src = patch->new_src = GIT_ITERATOR_TREE;
+		patch->old_src = patch->new_src = GIT_ITERATOR_TYPE_TREE;
 	}
 }
 
@@ -578,7 +578,7 @@ static int diff_patch_load(
 	 */
 
 	if ((delta->old_file.flags & GIT_DIFF_FILE_NO_DATA) == 0 &&
-		patch->old_src == GIT_ITERATOR_WORKDIR) {
+		patch->old_src == GIT_ITERATOR_TYPE_WORKDIR) {
 		if ((error = get_workdir_content(
 				ctxt, delta, &delta->old_file, &patch->old_data)) < 0)
 			goto cleanup;
@@ -587,7 +587,7 @@ static int diff_patch_load(
 	}
 
 	if ((delta->new_file.flags & GIT_DIFF_FILE_NO_DATA) == 0 &&
-		patch->new_src == GIT_ITERATOR_WORKDIR) {
+		patch->new_src == GIT_ITERATOR_TYPE_WORKDIR) {
 		if ((error = get_workdir_content(
 				ctxt, delta, &delta->new_file, &patch->new_data)) < 0)
 			goto cleanup;
@@ -596,7 +596,7 @@ static int diff_patch_load(
 	}
 
 	if ((delta->old_file.flags & GIT_DIFF_FILE_NO_DATA) == 0 &&
-		patch->old_src != GIT_ITERATOR_WORKDIR) {
+		patch->old_src != GIT_ITERATOR_TYPE_WORKDIR) {
 		if ((error = get_blob_content(
 				ctxt, delta, &delta->old_file,
 				&patch->old_data, &patch->old_blob)) < 0)
@@ -606,7 +606,7 @@ static int diff_patch_load(
 	}
 
 	if ((delta->new_file.flags & GIT_DIFF_FILE_NO_DATA) == 0 &&
-		patch->new_src != GIT_ITERATOR_WORKDIR) {
+		patch->new_src != GIT_ITERATOR_TYPE_WORKDIR) {
 		if ((error = get_blob_content(
 				ctxt, delta, &delta->new_file,
 				&patch->new_data, &patch->new_blob)) < 0)
diff --git a/src/iterator.c b/src/iterator.c
index 3d75dd8b5..a9df39bb8 100644
--- a/src/iterator.c
+++ b/src/iterator.c
@@ -24,12 +24,11 @@
 #define ITERATOR_BASE_INIT(P,NAME_LC,NAME_UC) do { \
 	(P) = git__calloc(1, sizeof(NAME_LC ## _iterator)); \
 	GITERR_CHECK_ALLOC(P); \
-	(P)->base.type    = GIT_ITERATOR_ ## NAME_UC; \
+	(P)->base.type    = GIT_ITERATOR_TYPE_ ## NAME_UC; \
 	(P)->base.cb    = &(P)->cb; \
 	ITERATOR_SET_CB(P,NAME_LC); \
 	(P)->base.start   = start ? git__strdup(start) : NULL; \
 	(P)->base.end     = end ? git__strdup(end) : NULL; \
-	(P)->base.ignore_case = false; \
 	if ((start && !(P)->base.start) || (end && !(P)->base.end)) { \
 		git__free(P); return -1; } \
 	} while (0)
@@ -54,6 +53,31 @@ static int iterator__reset_range(
 	return 0;
 }
 
+static int iterator_update_ignore_case(
+	git_iterator *iter,
+	git_iterator_flag_t flags)
+{
+	int error = 0, ignore_case = -1;
+
+	if ((flags & GIT_ITERATOR_IGNORE_CASE) != 0)
+		ignore_case = true;
+	else if ((flags & GIT_ITERATOR_DONT_IGNORE_CASE) != 0)
+		ignore_case = false;
+	else {
+		git_index *index;
+
+		if (!(error = git_repository_index__weakptr(&index, iter->repo)))
+			ignore_case = (index->ignore_case != false);
+	}
+
+	if (ignore_case > 0)
+		iter->flags = (iter->flags | GIT_ITERATOR_IGNORE_CASE);
+	else if (ignore_case == 0)
+		iter->flags = (iter->flags & ~GIT_ITERATOR_IGNORE_CASE);
+
+	return error;
+}
+
 static int empty_iterator__no_item(
 	git_iterator *iter, const git_index_entry **entry)
 {
@@ -91,13 +115,14 @@ typedef struct {
 	git_iterator_callbacks cb;
 } empty_iterator;
 
-int git_iterator_for_nothing(git_iterator **iter)
+int git_iterator_for_nothing(git_iterator **iter, git_iterator_flag_t flags)
 {
 	empty_iterator *i = git__calloc(1, sizeof(empty_iterator));
 	GITERR_CHECK_ALLOC(i);
 
-	i->base.type  = GIT_ITERATOR_EMPTY;
+	i->base.type  = GIT_ITERATOR_TYPE_EMPTY;
 	i->base.cb    = &i->cb;
+	i->base.flags = flags;
 	i->cb.current = empty_iterator__no_item;
 	i->cb.at_end  = empty_iterator__at_end;
 	i->cb.advance = empty_iterator__no_item;
@@ -349,6 +374,7 @@ static int tree_iterator__reset(
 int git_iterator_for_tree_range(
 	git_iterator **iter,
 	git_tree *tree,
+	git_iterator_flag_t flags,
 	const char *start,
 	const char *end)
 {
@@ -356,7 +382,7 @@ int git_iterator_for_tree_range(
 	tree_iterator *ti;
 
 	if (tree == NULL)
-		return git_iterator_for_nothing(iter);
+		return git_iterator_for_nothing(iter, flags);
 
 	if ((error = git_tree__dup(&tree, tree)) < 0)
 		return error;
@@ -364,13 +390,23 @@ int git_iterator_for_tree_range(
 	ITERATOR_BASE_INIT(ti, tree, TREE);
 
 	ti->base.repo = git_tree_owner(tree);
+
+	if ((error = iterator_update_ignore_case((git_iterator *)ti, flags)) < 0)
+		goto fail;
+
+	/* TODO: implement icase support natively in tree iterators */
+	ti->base.flags = (ti->base.flags & ~GIT_ITERATOR_IGNORE_CASE);
+
 	ti->stack = ti->tail = tree_iterator__alloc_frame(tree, ti->base.start);
 
 	if ((error = tree_iterator__expand_tree(ti)) < 0)
-		git_iterator_free((git_iterator *)ti);
-	else
-		*iter = (git_iterator *)ti;
+		goto fail;
 
+	*iter = (git_iterator *)ti;
+	return 0;
+
+fail:
+	git_iterator_free((git_iterator *)ti);
 	return error;
 }
 
@@ -466,15 +502,19 @@ static void index_iterator__free(git_iterator *self)
 int git_iterator_for_index_range(
 	git_iterator **iter,
 	git_index  *index,
+	git_iterator_flag_t flags,
 	const char *start,
 	const char *end)
 {
 	index_iterator *ii;
 
+	GIT_UNUSED(flags);
+
 	ITERATOR_BASE_INIT(ii, index, INDEX);
 
 	ii->base.repo = git_index_owner(index);
-	ii->base.ignore_case = index->ignore_case;
+	if (index->ignore_case)
+		ii->base.flags |= GIT_ITERATOR_IGNORE_CASE;
 	ii->index = index;
 	GIT_REFCOUNT_INC(index);
 
@@ -530,7 +570,8 @@ static workdir_iterator_frame *workdir_iterator__alloc_frame(
 	workdir_iterator *wi)
 {
 	workdir_iterator_frame *wf = git__calloc(1, sizeof(workdir_iterator_frame));
-	git_vector_cmp entry_compare = CASESELECT(wi->base.ignore_case,
+	git_vector_cmp entry_compare = CASESELECT(
+		(wi->base.flags & GIT_ITERATOR_IGNORE_CASE) != 0,
 		git_path_with_stat_cmp_icase, git_path_with_stat_cmp);
 
 	if (wf == NULL)
@@ -592,7 +633,8 @@ static int workdir_iterator__expand_dir(workdir_iterator *wi)
 	GITERR_CHECK_ALLOC(wf);
 
 	error = git_path_dirload_with_stat(
-		wi->path.ptr, wi->root_len, wi->base.ignore_case,
+		wi->path.ptr, wi->root_len,
+		(wi->base.flags & GIT_ITERATOR_IGNORE_CASE) != 0,
 		wi->base.start, wi->base.end, &wf->entries);
 
 	if (error < 0 || wf->entries.length == 0) {
@@ -775,12 +817,12 @@ static int workdir_iterator__update_entry(workdir_iterator *wi)
 int git_iterator_for_workdir_range(
 	git_iterator **iter,
 	git_repository *repo,
+	git_iterator_flag_t flags,
 	const char *start,
 	const char *end)
 {
 	int error;
 	workdir_iterator *wi;
-	git_index *index;
 
 	assert(iter && repo);
 
@@ -791,13 +833,8 @@ int git_iterator_for_workdir_range(
 	ITERATOR_BASE_INIT(wi, workdir, WORKDIR);
 	wi->base.repo = repo;
 
-	if ((error = git_repository_index__weakptr(&index, repo)) < 0) {
-		git_iterator_free((git_iterator *)wi);
-		return error;
-	}
-
-	/* Match ignore_case flag for iterator to that of the index */
-	wi->base.ignore_case = index->ignore_case;
+	if ((error = iterator_update_ignore_case((git_iterator *)wi, flags)) < 0)
+		goto fail;
 
 	if (git_buf_sets(&wi->path, git_repository_workdir(repo)) < 0 ||
 		git_path_to_dir(&wi->path) < 0 ||
@@ -808,23 +845,24 @@ int git_iterator_for_workdir_range(
 	}
 
 	wi->root_len = wi->path.size;
-	wi->entrycmp = wi->base.ignore_case ?
+	wi->entrycmp = (wi->base.flags & GIT_ITERATOR_IGNORE_CASE) != 0 ?
 		workdir_iterator__entry_cmp_icase : workdir_iterator__entry_cmp_case;
 
 	if ((error = workdir_iterator__expand_dir(wi)) < 0) {
-		if (error == GIT_ENOTFOUND)
-			error = 0;
-		else {
-			git_iterator_free((git_iterator *)wi);
-			wi = NULL;
-		}
+		if (error != GIT_ENOTFOUND)
+			goto fail;
+		giterr_clear();
 	}
 
 	*iter = (git_iterator *)wi;
+	return 0;
 
+fail:
+	git_iterator_free((git_iterator *)wi);
 	return error;
 }
 
+
 typedef struct {
 	/* replacement callbacks */
 	git_iterator_callbacks cb;
@@ -899,12 +937,12 @@ void git_iterator_spoolandsort_pop(git_iterator *self)
 {
 	spoolandsort_callbacks *scb = (spoolandsort_callbacks *)self->cb;
 
-	if (self->type != GIT_ITERATOR_SPOOLANDSORT)
+	if (self->type != GIT_ITERATOR_TYPE_SPOOLANDSORT)
 		return;
 
 	self->cb   = scb->orig;
 	self->type = scb->orig_type;
-	self->ignore_case = !self->ignore_case;
+	self->flags ^= GIT_ITERATOR_IGNORE_CASE;
 
 	spoolandsort_iterator__free_callbacks(scb);
 }
@@ -921,7 +959,7 @@ int git_iterator_spoolandsort_push(git_iterator *iter, bool ignore_case)
 	spoolandsort_callbacks *scb;
 	int (*entrycomp)(const void *a, const void *b);
 
-	if (iter->ignore_case == ignore_case)
+	if (((iter->flags & GIT_ITERATOR_IGNORE_CASE) != 0) == (ignore_case != 0))
 		return 0;
 
 	scb = git__calloc(1, sizeof(spoolandsort_callbacks));
@@ -964,8 +1002,8 @@ int git_iterator_spoolandsort_push(git_iterator *iter, bool ignore_case)
 	git_vector_sort(&scb->entries);
 
 	iter->cb   = (git_iterator_callbacks *)scb;
-	iter->type = GIT_ITERATOR_SPOOLANDSORT;
-	iter->ignore_case = !iter->ignore_case;
+	iter->type = GIT_ITERATOR_TYPE_SPOOLANDSORT;
+	iter->flags ^= GIT_ITERATOR_IGNORE_CASE;
 
 	return 0;
 
@@ -992,11 +1030,11 @@ void git_iterator_free(git_iterator *iter)
 
 git_index *git_iterator_index_get_index(git_iterator *iter)
 {
-	if (iter->type == GIT_ITERATOR_INDEX)
+	if (iter->type == GIT_ITERATOR_TYPE_INDEX)
 		return ((index_iterator *)iter)->index;
 
-	if (iter->type == GIT_ITERATOR_SPOOLANDSORT &&
-		((spoolandsort_callbacks *)iter->cb)->orig_type == GIT_ITERATOR_INDEX)
+	if (iter->type == GIT_ITERATOR_TYPE_SPOOLANDSORT &&
+		((spoolandsort_callbacks *)iter->cb)->orig_type == GIT_ITERATOR_TYPE_INDEX)
 		return ((index_iterator *)iter)->index;
 
 	return NULL;
@@ -1004,7 +1042,7 @@ git_index *git_iterator_index_get_index(git_iterator *iter)
 
 git_iterator_type_t git_iterator_inner_type(git_iterator *iter)
 {
-	if (iter->type == GIT_ITERATOR_SPOOLANDSORT)
+	if (iter->type == GIT_ITERATOR_TYPE_SPOOLANDSORT)
 		return ((spoolandsort_callbacks *)iter->cb)->orig_type;
 
 	return iter->type;
@@ -1013,7 +1051,7 @@ git_iterator_type_t git_iterator_inner_type(git_iterator *iter)
 int git_iterator_current_tree_entry(
 	git_iterator *iter, const git_tree_entry **tree_entry)
 {
-	*tree_entry = (iter->type != GIT_ITERATOR_TREE) ? NULL :
+	*tree_entry = (iter->type != GIT_ITERATOR_TYPE_TREE) ? NULL :
 		tree_iterator__tree_entry((tree_iterator *)iter);
 	return 0;
 }
@@ -1027,7 +1065,7 @@ int git_iterator_current_parent_tree(
 	tree_iterator_frame *tf;
 	const char *scan = parent_path;
 
-	if (iter->type != GIT_ITERATOR_TREE || ti->stack == NULL)
+	if (iter->type != GIT_ITERATOR_TYPE_TREE || ti->stack == NULL)
 		goto notfound;
 
 	for (tf = ti->tail; tf != NULL; tf = tf->prev) {
@@ -1061,7 +1099,7 @@ int git_iterator_current_is_ignored(git_iterator *iter)
 {
 	workdir_iterator *wi = (workdir_iterator *)iter;
 
-	if (iter->type != GIT_ITERATOR_WORKDIR)
+	if (iter->type != GIT_ITERATOR_TYPE_WORKDIR)
 		return 0;
 
 	if (wi->is_ignored != -1)
@@ -1078,7 +1116,7 @@ int git_iterator_advance_into_directory(
 {
 	workdir_iterator *wi = (workdir_iterator *)iter;
 
-	if (iter->type == GIT_ITERATOR_WORKDIR &&
+	if (iter->type == GIT_ITERATOR_TYPE_WORKDIR &&
 		wi->entry.path &&
 		(wi->entry.mode == GIT_FILEMODE_TREE ||
 		 wi->entry.mode == GIT_FILEMODE_COMMIT))
@@ -1112,7 +1150,7 @@ int git_iterator_current_workdir_path(git_iterator *iter, git_buf **path)
 {
 	workdir_iterator *wi = (workdir_iterator *)iter;
 
-	if (iter->type != GIT_ITERATOR_WORKDIR || !wi->entry.path)
+	if (iter->type != GIT_ITERATOR_TYPE_WORKDIR || !wi->entry.path)
 		*path = NULL;
 	else
 		*path = &wi->path;
diff --git a/src/iterator.h b/src/iterator.h
index 727da97b3..67e8a42dd 100644
--- a/src/iterator.h
+++ b/src/iterator.h
@@ -12,20 +12,26 @@
 #include "vector.h"
 #include "buffer.h"
 
-#define ITERATOR_PREFIXCMP(ITER, STR, PREFIX)	(((ITER).ignore_case) ? \
+#define ITERATOR_PREFIXCMP(ITER, STR, PREFIX)	\
+	(((ITER).flags & GIT_ITERATOR_IGNORE_CASE) != 0 ? \
 	git__prefixcmp_icase((STR), (PREFIX)) : \
 	git__prefixcmp((STR), (PREFIX)))
 
 typedef struct git_iterator git_iterator;
 
 typedef enum {
-	GIT_ITERATOR_EMPTY = 0,
-	GIT_ITERATOR_TREE = 1,
-	GIT_ITERATOR_INDEX = 2,
-	GIT_ITERATOR_WORKDIR = 3,
-	GIT_ITERATOR_SPOOLANDSORT = 4
+	GIT_ITERATOR_TYPE_EMPTY = 0,
+	GIT_ITERATOR_TYPE_TREE = 1,
+	GIT_ITERATOR_TYPE_INDEX = 2,
+	GIT_ITERATOR_TYPE_WORKDIR = 3,
+	GIT_ITERATOR_TYPE_SPOOLANDSORT = 4
 } git_iterator_type_t;
 
+typedef enum {
+	GIT_ITERATOR_IGNORE_CASE = (1 << 0), /* ignore_case */
+	GIT_ITERATOR_DONT_IGNORE_CASE = (1 << 1), /* force ignore_case off */
+} git_iterator_flag_t;
+
 typedef struct {
 	int (*current)(git_iterator *, const git_index_entry **);
 	int (*at_end)(git_iterator *);
@@ -41,33 +47,55 @@ struct git_iterator {
 	git_repository *repo;
 	char *start;
 	char *end;
-	bool ignore_case;
+	unsigned int flags;
 };
 
-extern int git_iterator_for_nothing(git_iterator **out);
+extern int git_iterator_for_nothing(
+	git_iterator **out, git_iterator_flag_t flags);
 
+/* tree iterators will match the ignore_case value from the index of the
+ * repository, unless you override with a non-zero flag value
+ */
 extern int git_iterator_for_tree_range(
-	git_iterator **out, git_tree *tree, const char *start, const char *end);
+	git_iterator **out,
+	git_tree *tree,
+	git_iterator_flag_t flags,
+	const char *start,
+	const char *end);
 
 GIT_INLINE(int) git_iterator_for_tree(git_iterator **out, git_tree *tree)
 {
-	return git_iterator_for_tree_range(out, tree, NULL, NULL);
+	return git_iterator_for_tree_range(out, tree, 0, NULL, NULL);
 }
 
+/* index iterators will take the ignore_case value from the index; the
+ * ignore_case flags are not used
+ */
 extern int git_iterator_for_index_range(
-	git_iterator **out, git_index *index, const char *start, const char *end);
+	git_iterator **out,
+	git_index *index,
+	git_iterator_flag_t flags,
+	const char *start,
+	const char *end);
 
 GIT_INLINE(int) git_iterator_for_index(git_iterator **out, git_index *index)
 {
-	return git_iterator_for_index_range(out, index, NULL, NULL);
+	return git_iterator_for_index_range(out, index, 0, NULL, NULL);
 }
 
+/* workdir iterators will match the ignore_case value from the index of the
+ * repository, unless you override with a non-zero flag value
+ */
 extern int git_iterator_for_workdir_range(
-	git_iterator **out, git_repository *repo, const char *start, const char *end);
+	git_iterator **out,
+	git_repository *repo,
+	git_iterator_flag_t flags,
+	const char *start,
+	const char *end);
 
 GIT_INLINE(int) git_iterator_for_workdir(git_iterator **out, git_repository *repo)
 {
-	return git_iterator_for_workdir_range(out, repo, NULL, NULL);
+	return git_iterator_for_workdir_range(out, repo, 0, NULL, NULL);
 }
 
 extern void git_iterator_free(git_iterator *iter);
@@ -127,6 +155,16 @@ GIT_INLINE(git_repository *) git_iterator_owner(git_iterator *iter)
 	return iter->repo;
 }
 
+GIT_INLINE(git_iterator_flag_t) git_iterator_flags(git_iterator *iter)
+{
+	return iter->flags;
+}
+
+GIT_INLINE(bool) git_iterator_ignore_case(git_iterator *iter)
+{
+	return ((iter->flags & GIT_ITERATOR_IGNORE_CASE) != 0);
+}
+
 extern int git_iterator_current_tree_entry(
 	git_iterator *iter, const git_tree_entry **tree_entry);
 
diff --git a/tests-clar/diff/iterator.c b/tests-clar/diff/iterator.c
index de083ea36..6fc5730bc 100644
--- a/tests-clar/diff/iterator.c
+++ b/tests-clar/diff/iterator.c
@@ -35,7 +35,8 @@ static void tree_iterator_test(
 	git_repository *repo = cl_git_sandbox_init(sandbox);
 
 	cl_assert(t = resolve_commit_oid_to_tree(repo, treeish));
-	cl_git_pass(git_iterator_for_tree_range(&i, t, start, end));
+	cl_git_pass(git_iterator_for_tree_range(
+		&i, t, GIT_ITERATOR_DONT_IGNORE_CASE, start, end));
 
 	/* test loop */
 	cl_git_pass(git_iterator_current(i, &entry));
@@ -304,7 +305,8 @@ void test_diff_iterator__tree_special_functions(void)
 		repo, "24fa9a9fc4e202313e24b648087495441dab432b");
 	cl_assert(t != NULL);
 
-	cl_git_pass(git_iterator_for_tree_range(&i, t, NULL, NULL));
+	cl_git_pass(git_iterator_for_tree_range(
+		&i, t, GIT_ITERATOR_DONT_IGNORE_CASE, NULL, NULL));
 	cl_git_pass(git_iterator_current(i, &entry));
 
 	while (entry != NULL) {
@@ -362,7 +364,7 @@ static void index_iterator_test(
 	git_repository *repo = cl_git_sandbox_init(sandbox);
 
 	cl_git_pass(git_repository_index(&index, repo));
-	cl_git_pass(git_iterator_for_index_range(&i, index, start, end));
+	cl_git_pass(git_iterator_for_index_range(&i, index, 0, start, end));
 	cl_git_pass(git_iterator_current(i, &entry));
 
 	while (entry != NULL) {
@@ -536,7 +538,7 @@ static void workdir_iterator_test(
 	int count = 0, count_all = 0, count_all_post_reset = 0;
 	git_repository *repo = cl_git_sandbox_init(sandbox);
 
-	cl_git_pass(git_iterator_for_workdir_range(&i, repo, start, end));
+	cl_git_pass(git_iterator_for_workdir_range(&i, repo, 0, start, end));
 	cl_git_pass(git_iterator_current(i, &entry));
 
 	while (entry != NULL) {
@@ -734,7 +736,7 @@ void test_diff_iterator__workdir_builtin_ignores(void)
 	cl_git_mkfile("attr/sub/.git", "whatever");
 
 	cl_git_pass(
-		git_iterator_for_workdir_range(&i, repo, "dir", "sub/sub/file"));
+		git_iterator_for_workdir_range(&i, repo, 0, "dir", "sub/sub/file"));
 	cl_git_pass(git_iterator_current(i, &entry));
 
 	for (idx = 0; entry != NULL; ++idx) {