diff --git a/CHANGELOG.md b/CHANGELOG.md
index dd200332..bb7b8797 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,7 @@ This project adheres to [Semantic Versioning](https://semver.org/).
 - Added support for HTTP/2, and HTTP/3 protocols. ([#523](https://github.com/httpie/cli/issues/523), [#692](https://github.com/httpie/cli/issues/692), [#1531](https://github.com/httpie/cli/pull/1531))
 - Added support for early (informational) responses. ([#752](https://github.com/httpie/cli/issues/752)) ([#1531](https://github.com/httpie/cli/pull/1531))
 - Added support for IPv4/IPv6 enforcement with `-6` and `-4`. ([#94](https://github.com/httpie/cli/issues/94), [#1531](https://github.com/httpie/cli/pull/1531))
+- Added support for Happy Eyeballs algorithm via `--heb` flag (disabled by default). [#1599](https://github.com/httpie/cli/issues/1599) [#1531](https://github.com/httpie/cli/pull/1531)
 - Added support for alternative DNS resolvers via `--resolver`. DNS over HTTPS, DNS over TLS, DNS over QUIC, and DNS over UDP are accepted. ([#99](https://github.com/httpie/cli/issues/99), [#1531](https://github.com/httpie/cli/pull/1531))
 - Added support for binding to a specific network adapter with `--interface`. ([#1422](https://github.com/httpie/cli/issues/1422), [#1531](https://github.com/httpie/cli/pull/1531))
 - Added support for specifying the local port with `--local-port`. ([#1456](https://github.com/httpie/cli/issues/1456), [#1531](https://github.com/httpie/cli/pull/1531))
diff --git a/docs/README.md b/docs/README.md
index cddb8621..8d339be8 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -1970,6 +1970,17 @@ You can specify multiple entries, concatenated with a comma:
 $ https --resolver "pie.dev:10.10.4.1,re.pie.dev:10.10.8.1" pie.dev/get
 ```
 
+## Happy Eyeballs
+
+By default, when HTTPie establish the connection it asks for the IP(v4 or v6) records of
+the requested domain and then tries them sequentially preferring IPv6 by default. This
+may induce longer connection delays and in some case hangs due to an unresponsive endpoint.
+To concurrently try to connect to available IP(v4 or v6), set the following flag:
+
+```bash
+$ https --heb pie.dev/get
+```
+
 ## Network interface
 
 In order to bind emitted request from a specific network adapter you can use the `--interface` flag.
diff --git a/httpie/cli/definition.py b/httpie/cli/definition.py
index 2f6bf55c..44061593 100644
--- a/httpie/cli/definition.py
+++ b/httpie/cli/definition.py
@@ -864,6 +864,20 @@ network.add_argument(
 
     """
 )
+network.add_argument(
+    "--heb",
+    default=False,
+    dest="happy_eyeballs",
+    action="store_true",
+    short_help="Establish the connection using IETF Happy Eyeballs algorithm",
+    help="""
+    By default, when HTTPie establish the connection it asks for the IP(v4 or v6) records of
+    the requested domain and then tries them sequentially preferring IPv6 by default. This
+    may induce longer connection delays and in some case hangs due to an unresponsive endpoint.
+    To concurrently try to connect to available IP(v4 or v6), set this flag.
+
+    """
+)
 network.add_argument(
     "--resolver",
     default=[],
diff --git a/httpie/client.py b/httpie/client.py
index a771ac54..63c5bd72 100644
--- a/httpie/client.py
+++ b/httpie/client.py
@@ -118,6 +118,7 @@ def collect_messages(
         disable_ipv4=args.ipv6,
         source_address=source_address,
         quic_cache=env.config.quic_file,
+        happy_eyeballs=args.happy_eyeballs,
     )
 
     if args.disable_http3 is False and args.force_http3 is True:
@@ -237,6 +238,7 @@ def build_requests_session(
     disable_ipv6: bool = False,
     source_address: typing.Tuple[str, int] = None,
     quic_cache: typing.Optional[Path] = None,
+    happy_eyeballs: bool = False,
 ) -> niquests.Session:
     requests_session = niquests.Session()
 
@@ -260,6 +262,8 @@ def build_requests_session(
         source_address=source_address,
         disable_http1=disable_http1,
         disable_http2=disable_http2,
+        disable_http3=disable_http3,
+        happy_eyeballs=happy_eyeballs,
     )
     https_adapter = HTTPieHTTPSAdapter(
         ciphers=ciphers,
@@ -276,6 +280,7 @@ def build_requests_session(
         disable_ipv6=disable_ipv6,
         source_address=source_address,
         quic_cache_layer=requests_session.quic_cache_layer,
+        happy_eyeballs=happy_eyeballs,
     )
     requests_session.mount('http://', http_adapter)
     requests_session.mount('https://', https_adapter)
diff --git a/tests/test_network.py b/tests/test_network.py
index 0be34d04..44804700 100644
--- a/tests/test_network.py
+++ b/tests/test_network.py
@@ -36,3 +36,13 @@ def test_ensure_interface_and_port_parameters(httpbin):
 
     assert r.exit_status == 0
     assert HTTP_OK in r
+
+
+def test_happy_eyeballs(remote_httpbin_secure):
+    r = http(
+        "--heb",  # this will automatically and concurrently try IPv6 and IPv4 endpoints
+        remote_httpbin_secure + "/get",
+    )
+
+    assert r.exit_status == 0
+    assert HTTP_OK in r