diff --git a/smithy-build/src/main/java/software/amazon/smithy/build/SmithyBuildImpl.java b/smithy-build/src/main/java/software/amazon/smithy/build/SmithyBuildImpl.java
index 6efd2da3c72..6488aafd448 100644
--- a/smithy-build/src/main/java/software/amazon/smithy/build/SmithyBuildImpl.java
+++ b/smithy-build/src/main/java/software/amazon/smithy/build/SmithyBuildImpl.java
@@ -303,7 +303,7 @@ private ProjectionResult applyProjection(
             ProjectionConfig projection,
             ValidatedResult<Model> baseModel,
             List<ResolvedPlugin> resolvedPlugins
-    ) {
+    ) throws Throwable {
         Model resolvedModel = baseModel.unwrap();
         LOGGER.fine(() -> String.format("Creating the `%s` projection", projectionName));
 
@@ -351,6 +351,8 @@ private ProjectionResult applyProjection(
             LOGGER.fine(() -> String.format("No transforms to apply for projection %s", projectionName));
         }
 
+        // Keep track of the first error created by plugins to fail the build after all plugins have run.
+        Throwable firstPluginError = null;
         ProjectionResult.Builder resultBuilder = ProjectionResult.builder()
                 .projectionName(projectionName)
                 .model(projectedModel)
@@ -358,11 +360,24 @@ private ProjectionResult applyProjection(
 
         for (ResolvedPlugin resolvedPlugin : resolvedPlugins) {
             if (pluginFilter.test(resolvedPlugin.id.getArtifactName())) {
-                applyPlugin(projectionName, projection, baseProjectionDir, resolvedPlugin,
+                try {
+                    applyPlugin(projectionName, projection, baseProjectionDir, resolvedPlugin,
                             projectedModel, resolvedModel, modelResult, resultBuilder);
+                } catch (Throwable e) {
+                    if (firstPluginError == null) {
+                        firstPluginError = e;
+                    } else {
+                        // Only log subsequent errors, since the first one is thrown.
+                        LOGGER.severe(String.format("Plugin `%s` failed: %s", resolvedPlugin.id, e));
+                    }
+                }
             }
         }
 
+        if (firstPluginError != null) {
+            throw firstPluginError;
+        }
+
         return resultBuilder.build();
     }
 
diff --git a/smithy-build/src/test/java/software/amazon/smithy/build/SmithyBuildTest.java b/smithy-build/src/test/java/software/amazon/smithy/build/SmithyBuildTest.java
index 47398bdfcb7..f140b2d7005 100644
--- a/smithy-build/src/test/java/software/amazon/smithy/build/SmithyBuildTest.java
+++ b/smithy-build/src/test/java/software/amazon/smithy/build/SmithyBuildTest.java
@@ -34,6 +34,7 @@
 import java.nio.file.Files;
 import java.nio.file.Path;
 import java.nio.file.Paths;
+import java.util.ArrayList;
 import java.util.Comparator;
 import java.util.HashMap;
 import java.util.LinkedHashMap;
@@ -268,6 +269,62 @@ public void failsByDefaultForUnknownPlugins() throws Exception {
         assertThat(e.getMessage(), containsString("Unable to find a plugin for `unknown1`"));
     }
 
+    @Test
+    public void defersFailureUntilAfterAllPluginsApplied() throws Exception {
+        SmithyBuildConfig config = SmithyBuildConfig.builder()
+                .load(Paths.get(getClass().getResource("defers-failure.json").toURI()))
+                .outputDirectory(outputDirectory.toString())
+                .build();
+
+        RuntimeException canned = new RuntimeException("broken");
+
+        // "broken" will run before "test1Serial" because of natural ordering
+        Map<String, SmithyBuildPlugin> plugins = new HashMap<>();
+        plugins.put("broken", new SmithyBuildPlugin() {
+            @Override
+            public String getName() {
+                        return "broken";
+                    }
+            @Override
+            public void execute(PluginContext context) {
+                        throw canned;
+                    }
+        });
+        plugins.put("test1Serial", new Test1SerialPlugin());
+
+        Function<String, Optional<SmithyBuildPlugin>> factory = SmithyBuildPlugin.createServiceFactory();
+        Function<String, Optional<SmithyBuildPlugin>> composed = name -> OptionalUtils.or(
+                Optional.ofNullable(plugins.get(name)), () -> factory.apply(name));
+
+        // Because the build will fail, we need a way to access the file manifests
+        List<FileManifest> manifests = new ArrayList<>();
+        Function<Path, FileManifest> fileManifestFactory = pluginBaseDir -> {
+            FileManifest fileManifest = new MockManifest(pluginBaseDir);
+            manifests.add(fileManifest);
+            return fileManifest;
+        };
+
+        SmithyBuild builder = new SmithyBuild()
+                .pluginFactory(composed)
+                .fileManifestFactory(fileManifestFactory)
+                .config(config);
+
+        SmithyBuildException e = Assertions.assertThrows(SmithyBuildException.class, builder::build);
+
+        // "broken" plugin produces the error that causes the build to fail
+        assertThat(e.getMessage(), containsString("java.lang.RuntimeException: broken"));
+        assertThat(e.getSuppressed(), equalTo(new Throwable[]{canned}));
+
+        List<Path> files = manifests.stream()
+                .flatMap(fm -> fm.getFiles().stream())
+                .collect(Collectors.toList());
+        assertThat(files, containsInAnyOrder(
+                outputDirectory.resolve("source/sources/manifest"),
+                outputDirectory.resolve("source/model/model.json"),
+                outputDirectory.resolve("source/build-info/smithy-build-info.json"),
+                outputDirectory.resolve("source/test1Serial/hello1Serial")));
+    }
+
     @Test
     public void cannotSetFiltersOrMappersOnSourceProjection() {
         Throwable thrown = Assertions.assertThrows(SmithyBuildException.class, () -> {
diff --git a/smithy-build/src/test/resources/software/amazon/smithy/build/defers-failure.json b/smithy-build/src/test/resources/software/amazon/smithy/build/defers-failure.json
new file mode 100644
index 00000000000..de0651acf12
--- /dev/null
+++ b/smithy-build/src/test/resources/software/amazon/smithy/build/defers-failure.json
@@ -0,0 +1,7 @@
+{
+  "version": "2.0",
+  "plugins": {
+    "broken": {},
+    "test1Serial": {}
+  }
+}