diff --git a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/HttpApiConversions.java b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/HttpApiConversions.java
index 584944d32f..76ba9c242a 100644
--- a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/HttpApiConversions.java
+++ b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/HttpApiConversions.java
@@ -19,6 +19,8 @@
 import io.servicetalk.http.api.StreamingHttpClientToBlockingStreamingHttpClient.ReservedStreamingHttpConnectionToBlockingStreaming;
 import io.servicetalk.http.api.StreamingHttpClientToHttpClient.ReservedStreamingHttpConnectionToReservedHttpConnection;
 
+import static io.servicetalk.http.api.HttpContextKeys.HTTP_EXECUTION_STRATEGY_KEY;
+
 /**
  * Conversion routines to {@link StreamingHttpService}.
  */
@@ -486,4 +488,20 @@ public static HttpService toHttpService(StreamingHttpService service) {
     public static BlockingStreamingHttpService toBlockingStreamingHttpService(StreamingHttpService service) {
         return new StreamingHttpServiceToBlockingStreamingHttpService(service);
     }
+
+    /**
+     * Tries assigning a strategy for a request execution if none is already assigned.
+     * <p>
+     * Top level user-facing API can optimize execution strategy (offloading) when it's known that users won't interact
+     * with some parts of request-response processing.
+     *
+     * @param metaData request meta-data to assign the strategy to
+     * @param strategy {@link HttpExecutionStrategy} to assign
+     * @see <a href=
+     * "https://docs.servicetalk.io/servicetalk-http-api/SNAPSHOT/blocking-safe-by-default.html#programming-models">
+     * Programming models</a>
+     */
+    static void assignStrategy(final HttpRequestMetaData metaData, final HttpExecutionStrategy strategy) {
+        metaData.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
+    }
 }
diff --git a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingHttpClient.java b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingHttpClient.java
index 670ad24d7b..34ad25eeeb 100644
--- a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingHttpClient.java
+++ b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingHttpClient.java
@@ -18,7 +18,7 @@
 import io.servicetalk.concurrent.BlockingIterable;
 
 import static io.servicetalk.concurrent.api.internal.BlockingUtils.blockingInvocation;
-import static io.servicetalk.http.api.HttpContextKeys.HTTP_EXECUTION_STRATEGY_KEY;
+import static io.servicetalk.http.api.HttpApiConversions.assignStrategy;
 import static io.servicetalk.http.api.HttpExecutionStrategies.defaultStrategy;
 import static io.servicetalk.http.api.RequestResponseFactories.toAggregated;
 import static io.servicetalk.http.api.StreamingHttpConnectionToBlockingHttpConnection.DEFAULT_BLOCKING_CONNECTION_STRATEGY;
@@ -44,7 +44,7 @@ public HttpExecutionStrategy executionStrategy() {
 
     @Override
     public ReservedBlockingHttpConnection reserveConnection(final HttpRequestMetaData metaData) throws Exception {
-        metaData.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
+        assignStrategy(metaData, strategy);
         return blockingInvocation(client.reserveConnection(metaData)
                 .map(c -> new ReservedStreamingHttpConnectionToReservedBlockingHttpConnection(c, this.strategy,
                         reqRespFactory)));
@@ -57,7 +57,7 @@ public StreamingHttpClient asStreamingClient() {
 
     @Override
     public HttpResponse request(final HttpRequest request) throws Exception {
-        request.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
+        assignStrategy(request, strategy);
         return BlockingRequestUtils.request(client, request);
     }
 
@@ -89,6 +89,7 @@ public HttpRequest newRequest(final HttpRequestMethod method, final String reque
     static final class ReservedStreamingHttpConnectionToReservedBlockingHttpConnection implements
                                                                                        ReservedBlockingHttpConnection {
         private final ReservedStreamingHttpConnection connection;
+        private final HttpExecutionStrategy strategy;
         private final HttpConnectionContext context;
         private final HttpExecutionContext executionContext;
         private final HttpRequestResponseFactory reqRespFactory;
@@ -104,13 +105,13 @@ static final class ReservedStreamingHttpConnectionToReservedBlockingHttpConnecti
                 final HttpExecutionStrategy strategy,
                 final HttpRequestResponseFactory reqRespFactory) {
 
-            requireNonNull(strategy);
             this.connection = requireNonNull(connection);
+            this.strategy = requireNonNull(strategy);
             final HttpConnectionContext originalCtx = connection.connectionContext();
             executionContext = new DelegatingHttpExecutionContext(connection.executionContext()) {
                 @Override
                 public HttpExecutionStrategy executionStrategy() {
-                    return strategy;
+                    return ReservedStreamingHttpConnectionToReservedBlockingHttpConnection.this.strategy;
                 }
             };
             context = new DelegatingHttpConnectionContext(originalCtx) {
@@ -144,6 +145,7 @@ public <T> BlockingIterable<? extends T> transportEventIterable(final HttpEventK
 
         @Override
         public HttpResponse request(final HttpRequest request) throws Exception {
+            assignStrategy(request, strategy);
             return BlockingRequestUtils.request(connection, request);
         }
 
diff --git a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingStreamingHttpClient.java b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingStreamingHttpClient.java
index 7841b60032..cb7ad617a6 100644
--- a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingStreamingHttpClient.java
+++ b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToBlockingStreamingHttpClient.java
@@ -18,7 +18,7 @@
 import io.servicetalk.concurrent.BlockingIterable;
 
 import static io.servicetalk.concurrent.api.internal.BlockingUtils.blockingInvocation;
-import static io.servicetalk.http.api.HttpContextKeys.HTTP_EXECUTION_STRATEGY_KEY;
+import static io.servicetalk.http.api.HttpApiConversions.assignStrategy;
 import static io.servicetalk.http.api.HttpExecutionStrategies.defaultStrategy;
 import static io.servicetalk.http.api.RequestResponseFactories.toBlockingStreaming;
 import static io.servicetalk.http.api.StreamingHttpConnectionToBlockingStreamingHttpConnection.DEFAULT_BLOCKING_STREAMING_CONNECTION_STRATEGY;
@@ -46,9 +46,9 @@ public HttpExecutionStrategy executionStrategy() {
     @Override
     public ReservedBlockingStreamingHttpConnection reserveConnection(final HttpRequestMetaData metaData)
             throws Exception {
+        assignStrategy(metaData, strategy);
         // It is assumed that users will always apply timeouts at the StreamingHttpService layer (e.g. via filter).
         // So we don't apply any explicit timeout here and just wait forever.
-        metaData.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
         return blockingInvocation(client.reserveConnection(metaData)
                 .map(c -> new ReservedStreamingHttpConnectionToBlockingStreaming(c, this.strategy, reqRespFactory)));
     }
@@ -60,7 +60,7 @@ public StreamingHttpClient asStreamingClient() {
 
     @Override
     public BlockingStreamingHttpResponse request(final BlockingStreamingHttpRequest request) throws Exception {
-        request.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
+        assignStrategy(request, strategy);
         return blockingInvocation(client.request(request.toStreamingRequest())).toBlockingStreamingResponse();
     }
 
@@ -148,6 +148,7 @@ public <T> BlockingIterable<? extends T> transportEventIterable(final HttpEventK
 
         @Override
         public BlockingStreamingHttpResponse request(final BlockingStreamingHttpRequest request) throws Exception {
+            assignStrategy(request, strategy);
             return blockingInvocation(connection.request(request.toStreamingRequest()))
                     .toBlockingStreamingResponse();
         }
diff --git a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToHttpClient.java b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToHttpClient.java
index 5a9d73fc28..258fcc2335 100644
--- a/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToHttpClient.java
+++ b/servicetalk-http-api/src/main/java/io/servicetalk/http/api/StreamingHttpClientToHttpClient.java
@@ -19,7 +19,7 @@
 import io.servicetalk.concurrent.api.Publisher;
 import io.servicetalk.concurrent.api.Single;
 
-import static io.servicetalk.http.api.HttpContextKeys.HTTP_EXECUTION_STRATEGY_KEY;
+import static io.servicetalk.http.api.HttpApiConversions.assignStrategy;
 import static io.servicetalk.http.api.HttpExecutionStrategies.defaultStrategy;
 import static io.servicetalk.http.api.RequestResponseFactories.toAggregated;
 import static io.servicetalk.http.api.StreamingHttpConnectionToHttpConnection.DEFAULT_ASYNC_CONNECTION_STRATEGY;
@@ -46,7 +46,7 @@ public HttpExecutionStrategy executionStrategy() {
     @Override
     public Single<HttpResponse> request(final HttpRequest request) {
         return Single.defer(() -> {
-            request.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
+            assignStrategy(request, strategy);
             return client.request(request.toStreamingRequest())
                     .flatMap(response -> response.toResponse().shareContextOnSubscribe())
                     .shareContextOnSubscribe();
@@ -56,7 +56,7 @@ public Single<HttpResponse> request(final HttpRequest request) {
     @Override
     public Single<ReservedHttpConnection> reserveConnection(final HttpRequestMetaData metaData) {
         return Single.defer(() -> {
-            metaData.context().putIfAbsent(HTTP_EXECUTION_STRATEGY_KEY, strategy);
+            assignStrategy(metaData, strategy);
             return client.reserveConnection(metaData)
                     .map(c -> new ReservedStreamingHttpConnectionToReservedHttpConnection(c, this.strategy,
                             reqRespFactory))
@@ -170,8 +170,12 @@ public <T> Publisher<? extends T> transportEventStream(final HttpEventKey<T> eve
 
         @Override
         public Single<HttpResponse> request(final HttpRequest request) {
-            return connection.request(request.toStreamingRequest())
-                    .flatMap(response -> response.toResponse().shareContextOnSubscribe());
+            return Single.defer(() -> {
+                assignStrategy(request, strategy);
+                return connection.request(request.toStreamingRequest())
+                        .flatMap(response -> response.toResponse().shareContextOnSubscribe())
+                        .shareContextOnSubscribe();
+            });
         }
 
         @Override