diff --git a/CHANGELOG.md b/CHANGELOG.md
index 34dd3d9cc..3aa527a7e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,7 @@
 - Update Projection Extension to version 2 - proj:epsg -> proj:code ([#1287](https://github.com/stac-utils/pystac/pull/1287))
 - Update migrate code to handle license changes in STAC spec 1.1.0 ([#1491](https://github.com/stac-utils/pystac/pull/1491))
 - Allow links to have `file://` prefix - but don't write them that way by default ([#1489](https://github.com/stac-utils/pystac/pull/1489))
+- Raise `STACError` with message when a link is expected to resolve to a STAC object but doesn't ([#1500](https://github.com/stac-utils/pystac/pull/1500))
 
 ### Fixed
 
diff --git a/pystac/link.py b/pystac/link.py
index 916c8ec32..e82ddad5a 100644
--- a/pystac/link.py
+++ b/pystac/link.py
@@ -6,6 +6,7 @@
 from typing import TYPE_CHECKING, Any, TypeVar
 
 import pystac
+from pystac.errors import STACError
 from pystac.html.jinja_env import get_jinja_env
 from pystac.utils import (
     HREF as HREF,
@@ -327,8 +328,12 @@ def resolve_stac_object(self, root: Catalog | None = None) -> Link:
                                 stac_io = owner_root._stac_io
                     if stac_io is None:
                         stac_io = pystac.StacIO.default()
-
-                obj = stac_io.read_stac_object(target_href, root=root)
+                try:
+                    obj = stac_io.read_stac_object(target_href, root=root)
+                except Exception as e:
+                    raise STACError(
+                        f"HREF: '{target_href}' does not resolve to a STAC object"
+                    ) from e
                 obj.set_self_href(target_href)
                 if root is not None:
                     obj = root._resolved_objects.get_or_cache(obj)
diff --git a/tests/test_catalog.py b/tests/test_catalog.py
index 45b7aa536..1d76b0e84 100644
--- a/tests/test_catalog.py
+++ b/tests/test_catalog.py
@@ -24,6 +24,7 @@
     Item,
     MediaType,
 )
+from pystac.errors import STACError
 from pystac.layout import (
     BestPracticesLayoutStrategy,
     HrefLayoutStrategy,
@@ -674,7 +675,7 @@ def test_save_unresolved(self) -> None:
             assert len(os.listdir(temporary_directory)) == 2
 
         with tempfile.TemporaryDirectory() as temporary_directory:
-            with pytest.raises(FileNotFoundError):
+            with pytest.raises(STACError, match="does not resolve to a STAC object"):
                 catalog.normalize_and_save(temporary_directory, skip_unresolved=False)
 
     def test_generate_subcatalogs_works_with_custom_properties(self) -> None:
diff --git a/tests/test_link.py b/tests/test_link.py
index 0461a2598..aff1939fa 100644
--- a/tests/test_link.py
+++ b/tests/test_link.py
@@ -10,6 +10,7 @@
 
 import pystac
 from pystac import Collection, Item, Link
+from pystac.errors import STACError
 from pystac.link import HIERARCHICAL_LINKS
 from pystac.utils import make_posix_style
 from tests.utils.test_cases import ARBITRARY_EXTENT
@@ -98,6 +99,14 @@ def test_resolve_stac_object_no_root_and_target_is_item(self) -> None:
         link = pystac.Link("my rel", target=self.item)
         link.resolve_stac_object()
 
+    @pytest.mark.skipif(os.name == "nt", reason="Non-windows test")
+    def test_resolve_stac_object_throws_informative_error(self) -> None:
+        link = pystac.Link("root", target="/a/b/foo.json")
+        with pytest.raises(
+            STACError, match="HREF: '/a/b/foo.json' does not resolve to a STAC object"
+        ):
+            link.resolve_stac_object()
+
     def test_resolved_self_href(self) -> None:
         catalog = pystac.Catalog(id="test", description="test desc")
         with TemporaryDirectory() as temporary_directory: