diff --git a/asdf/_tests/test_extension.py b/asdf/_tests/test_extension.py
index fd7a0ec6d..f9b8baf50 100644
--- a/asdf/_tests/test_extension.py
+++ b/asdf/_tests/test_extension.py
@@ -3,11 +3,10 @@
 
 import pytest
 from packaging.specifiers import SpecifierSet
-from yaml.representer import RepresenterError
 
 import asdf
 from asdf import AsdfFile, config_context
-from asdf.exceptions import AsdfManifestURIMismatchWarning, AsdfWarning, ValidationError
+from asdf.exceptions import AsdfManifestURIMismatchWarning, AsdfSerializationError, AsdfWarning, ValidationError
 from asdf.extension import (
     Compressor,
     Converter,
@@ -578,7 +577,7 @@ class FooExtension(Extension):
     tree = {"obj": Foo()}
     with config_context() as cfg:
         cfg.add_extension(FooExtension())
-        with pytest.raises(RepresenterError, match=r"cannot represent an object"):
+        with pytest.raises(AsdfSerializationError, match=r"is not serializable by asdf"):
             roundtrip_object(tree)
 
 
diff --git a/asdf/_tests/test_yaml.py b/asdf/_tests/test_yaml.py
index 34598420c..55648dd46 100644
--- a/asdf/_tests/test_yaml.py
+++ b/asdf/_tests/test_yaml.py
@@ -10,7 +10,7 @@
 
 import asdf
 from asdf import tagged, treeutil, yamlutil
-from asdf.exceptions import AsdfConversionWarning, AsdfDeprecationWarning, AsdfWarning
+from asdf.exceptions import AsdfConversionWarning, AsdfDeprecationWarning, AsdfSerializationError, AsdfWarning
 from asdf.testing.helpers import yaml_to_asdf
 
 
@@ -104,7 +104,7 @@ class Foo:
 
     buff = io.BytesIO()
     ff = asdf.AsdfFile(tree)
-    with pytest.raises(yaml.YAMLError, match=r"\('cannot represent an object', .*\)"):
+    with pytest.raises(AsdfSerializationError, match=r".*is not serializable by asdf.*"):
         ff.write_to(buff)
 
 
@@ -350,7 +350,7 @@ class MyNDArray(np.ndarray):
 
     with asdf.config.config_context() as cfg:
         cfg.convert_unknown_ndarray_subclasses = False
-        with pytest.raises(yaml.representer.RepresenterError, match=r".*cannot represent.*"):
+        with pytest.raises(AsdfSerializationError, match=r".*is not serializable by asdf.*"):
             af.write_to(fn)
 
 
diff --git a/asdf/exceptions.py b/asdf/exceptions.py
index 879aa25c2..543be0987 100644
--- a/asdf/exceptions.py
+++ b/asdf/exceptions.py
@@ -1,3 +1,5 @@
+from yaml.representer import RepresenterError
+
 from asdf._jsonschema import ValidationError
 
 __all__ = [
@@ -73,3 +75,11 @@ class AsdfLazyReferenceError(ReferenceError):
     collected and you may need to update your code to keep the AsdfFile
     in memory (by keeping a reference).
     """
+
+
+class AsdfSerializationError(RepresenterError):
+    """
+    An object failed serialization by asdf and by yaml. This likely indicates
+    that the object does not have a supporting asdf Converter and needs to
+    be manually converted to a supported type.
+    """
diff --git a/asdf/yamlutil.py b/asdf/yamlutil.py
index b93ab3740..63c2d864a 100644
--- a/asdf/yamlutil.py
+++ b/asdf/yamlutil.py
@@ -7,7 +7,7 @@
 
 from . import config, schema, tagged, treeutil, util
 from .constants import STSCI_SCHEMA_TAG_BASE, YAML_TAG_PREFIX
-from .exceptions import AsdfConversionWarning
+from .exceptions import AsdfConversionWarning, AsdfSerializationError
 from .extension._serialization_context import BlockAccess
 from .tags.core import AsdfObject
 from .versioning import _YAML_VERSION, _yaml_base_loader
@@ -403,14 +403,26 @@ def dump_tree(tree, fd, ctx, tree_finalizer=None, _serialization_context=None):
                 if key not in tags:
                     tags[key] = val
 
-    yaml.dump_all(
-        [tree],
-        stream=fd,
-        Dumper=AsdfDumper,
-        explicit_start=True,
-        explicit_end=True,
-        version=_YAML_VERSION,
-        allow_unicode=True,
-        encoding="utf-8",
-        tags=tags,
-    )
+    try:
+        yaml.dump_all(
+            [tree],
+            stream=fd,
+            Dumper=AsdfDumper,
+            explicit_start=True,
+            explicit_end=True,
+            version=_YAML_VERSION,
+            allow_unicode=True,
+            encoding="utf-8",
+            tags=tags,
+        )
+    except yaml.representer.RepresenterError as err:
+        if len(err.args) < 2:
+            raise err
+        # inspect the exception arguments to determine what object failed
+        obj = err.args[1]
+        msg = (
+            f"Object of type[{type(obj)}] is not serializable by asdf. "
+            "Please convert the object to a supported type or implement "
+            "a Converter for this type to allow the tree to be serialized."
+        )
+        raise AsdfSerializationError(msg, obj) from err