diff --git a/bloom.c b/bloom.c
index 739fa093ba..24dd874e46 100644
--- a/bloom.c
+++ b/bloom.c
@@ -7,6 +7,9 @@
 #include "commit-graph.h"
 #include "commit.h"
 #include "commit-slab.h"
+#include "tree.h"
+#include "tree-walk.h"
+#include "config.h"
 
 define_commit_slab(bloom_filter_slab, struct bloom_filter);
 
@@ -250,6 +253,73 @@ static void init_truncated_large_filter(struct bloom_filter *filter,
 	filter->version = version;
 }
 
+#define VISITED   (1u<<21)
+#define HIGH_BITS (1u<<22)
+
+static int has_entries_with_high_bit(struct repository *r, struct tree *t)
+{
+	if (parse_tree(t))
+		return 1;
+
+	if (!(t->object.flags & VISITED)) {
+		struct tree_desc desc;
+		struct name_entry entry;
+
+		init_tree_desc(&desc, t->buffer, t->size);
+		while (tree_entry(&desc, &entry)) {
+			size_t i;
+			for (i = 0; i < entry.pathlen; i++) {
+				if (entry.path[i] & 0x80) {
+					t->object.flags |= HIGH_BITS;
+					goto done;
+				}
+			}
+
+			if (S_ISDIR(entry.mode)) {
+				struct tree *sub = lookup_tree(r, &entry.oid);
+				if (sub && has_entries_with_high_bit(r, sub)) {
+					t->object.flags |= HIGH_BITS;
+					goto done;
+				}
+			}
+
+		}
+
+done:
+		t->object.flags |= VISITED;
+	}
+
+	return !!(t->object.flags & HIGH_BITS);
+}
+
+static int commit_tree_has_high_bit_paths(struct repository *r,
+					  struct commit *c)
+{
+	struct tree *t;
+	if (repo_parse_commit(r, c))
+		return 1;
+	t = repo_get_commit_tree(r, c);
+	if (!t)
+		return 1;
+	return has_entries_with_high_bit(r, t);
+}
+
+static struct bloom_filter *upgrade_filter(struct repository *r, struct commit *c,
+					   struct bloom_filter *filter,
+					   int hash_version)
+{
+	struct commit_list *p = c->parents;
+	if (commit_tree_has_high_bit_paths(r, c))
+		return NULL;
+
+	if (p && commit_tree_has_high_bit_paths(r, p->item))
+		return NULL;
+
+	filter->version = hash_version;
+
+	return filter;
+}
+
 struct bloom_filter *get_bloom_filter(struct repository *r, struct commit *c)
 {
 	struct bloom_filter *filter;
@@ -292,9 +362,23 @@ struct bloom_filter *get_or_compute_bloom_filter(struct repository *r,
 						     filter, graph_pos);
 	}
 
-	if ((filter->data && filter->len) &&
-	    (!settings || settings->hash_version == filter->version))
-		return filter;
+	if (filter->data && filter->len) {
+		struct bloom_filter *upgrade;
+		if (!settings || settings->hash_version == filter->version)
+			return filter;
+
+		/* version mismatch, see if we can upgrade */
+		if (compute_if_not_present &&
+		    git_env_bool("GIT_TEST_UPGRADE_BLOOM_FILTERS", 1)) {
+			upgrade = upgrade_filter(r, c, filter,
+						 settings->hash_version);
+			if (upgrade) {
+				if (computed)
+					*computed |= BLOOM_UPGRADED;
+				return upgrade;
+			}
+		}
+	}
 	if (!compute_if_not_present)
 		return NULL;
 
diff --git a/bloom.h b/bloom.h
index bfe389e29c..e3a9b68905 100644
--- a/bloom.h
+++ b/bloom.h
@@ -102,6 +102,7 @@ enum bloom_filter_computed {
 	BLOOM_COMPUTED     = (1 << 1),
 	BLOOM_TRUNC_LARGE  = (1 << 2),
 	BLOOM_TRUNC_EMPTY  = (1 << 3),
+	BLOOM_UPGRADED     = (1 << 4),
 };
 
 struct bloom_filter *get_or_compute_bloom_filter(struct repository *r,
diff --git a/commit-graph.c b/commit-graph.c
index b70d57b085..50dcbb4d9b 100644
--- a/commit-graph.c
+++ b/commit-graph.c
@@ -1102,6 +1102,7 @@ struct write_commit_graph_context {
 	int count_bloom_filter_not_computed;
 	int count_bloom_filter_trunc_empty;
 	int count_bloom_filter_trunc_large;
+	int count_bloom_filter_upgraded;
 };
 
 static int write_graph_chunk_fanout(struct hashfile *f,
@@ -1709,6 +1710,8 @@ static void trace2_bloom_filter_write_statistics(struct write_commit_graph_conte
 			   ctx->count_bloom_filter_trunc_empty);
 	trace2_data_intmax("commit-graph", ctx->r, "filter-trunc-large",
 			   ctx->count_bloom_filter_trunc_large);
+	trace2_data_intmax("commit-graph", ctx->r, "filter-upgraded",
+			   ctx->count_bloom_filter_upgraded);
 }
 
 static void compute_bloom_filters(struct write_commit_graph_context *ctx)
@@ -1750,6 +1753,8 @@ static void compute_bloom_filters(struct write_commit_graph_context *ctx)
 				ctx->count_bloom_filter_trunc_empty++;
 			if (computed & BLOOM_TRUNC_LARGE)
 				ctx->count_bloom_filter_trunc_large++;
+		} else if (computed & BLOOM_UPGRADED) {
+			ctx->count_bloom_filter_upgraded++;
 		} else if (computed & BLOOM_NOT_COMPUTED)
 			ctx->count_bloom_filter_not_computed++;
 		ctx->total_bloom_filter_data_size += filter
diff --git a/object.h b/object.h
index db25714b4e..2e5e08725f 100644
--- a/object.h
+++ b/object.h
@@ -75,6 +75,7 @@ void object_array_init(struct object_array *array);
  * commit-reach.c:                                  16-----19
  * sha1-name.c:                                              20
  * list-objects-filter.c:                                      21
+ * bloom.c:                                                    2122
  * builtin/fsck.c:           0--3
  * builtin/gc.c:             0
  * builtin/index-pack.c:                                     2021
diff --git a/t/t4216-log-bloom.sh b/t/t4216-log-bloom.sh
index 68066b7928..569f2b6f8b 100755
--- a/t/t4216-log-bloom.sh
+++ b/t/t4216-log-bloom.sh
@@ -221,6 +221,10 @@ test_filter_trunc_large () {
 	grep "\"key\":\"filter-trunc-large\",\"value\":\"$1\"" $2
 }
 
+test_filter_upgraded () {
+	grep "\"key\":\"filter-upgraded\",\"value\":\"$1\"" $2
+}
+
 test_expect_success 'correctly report changes over limit' '
 	git init limits &&
 	(
@@ -628,7 +632,13 @@ test_expect_success 'when writing another commit graph, preserve existing versio
 test_expect_success 'when writing commit graph, do not reuse changed-path of another version' '
 	git init doublewrite &&
 	test_commit -C doublewrite c "$CENT" &&
+
 	git -C doublewrite config --add commitgraph.changedPathsVersion 1 &&
+	GIT_TRACE2_EVENT="$(pwd)/trace2.txt" \
+		git -C doublewrite commit-graph write --reachable --changed-paths &&
+	test_filter_computed 1 trace2.txt &&
+	test_filter_upgraded 0 trace2.txt &&
+
 	git -C doublewrite commit-graph write --reachable --changed-paths &&
 	for v in -2 3
 	do
@@ -639,8 +649,13 @@ test_expect_success 'when writing commit graph, do not reuse changed-path of ano
 		EOF
 		test_cmp expect err || return 1
 	done &&
+
 	git -C doublewrite config --add commitgraph.changedPathsVersion 2 &&
-	git -C doublewrite commit-graph write --reachable --changed-paths &&
+	GIT_TRACE2_EVENT="$(pwd)/trace2.txt" \
+		git -C doublewrite commit-graph write --reachable --changed-paths &&
+	test_filter_computed 1 trace2.txt &&
+	test_filter_upgraded 0 trace2.txt &&
+
 	(
 		cd doublewrite &&
 		echo "c01f" >expect &&
@@ -649,4 +664,22 @@ test_expect_success 'when writing commit graph, do not reuse changed-path of ano
 	)
 '
 
+test_expect_success 'when writing commit graph, reuse changed-path of another version where possible' '
+	git init upgrade &&
+
+	test_commit -C upgrade base no-high-bits &&
+
+	git -C upgrade config --add commitgraph.changedPathsVersion 1 &&
+	GIT_TRACE2_EVENT="$(pwd)/trace2.txt" \
+		git -C upgrade commit-graph write --reachable --changed-paths &&
+	test_filter_computed 1 trace2.txt &&
+	test_filter_upgraded 0 trace2.txt &&
+
+	git -C upgrade config --add commitgraph.changedPathsVersion 2 &&
+	GIT_TRACE2_EVENT="$(pwd)/trace2.txt" \
+		git -C upgrade commit-graph write --reachable --changed-paths &&
+	test_filter_computed 0 trace2.txt &&
+	test_filter_upgraded 1 trace2.txt
+'
+
 test_done