diff --git a/src/poetry/console/exceptions.py b/src/poetry/console/exceptions.py
index 888a27e728f..21385251715 100644
--- a/src/poetry/console/exceptions.py
+++ b/src/poetry/console/exceptions.py
@@ -222,3 +222,9 @@ def create(
             )
 
         return cls(reason, messages)
+
+    def append(self, message: str | ConsoleMessage) -> PoetryRuntimeError:
+        if isinstance(message, str):
+            message = ConsoleMessage(message)
+        self._messages.append(message)
+        return self
diff --git a/src/poetry/utils/authenticator.py b/src/poetry/utils/authenticator.py
index b51a44c0c59..05b83a5400b 100644
--- a/src/poetry/utils/authenticator.py
+++ b/src/poetry/utils/authenticator.py
@@ -22,6 +22,8 @@
 
 from poetry.__version__ import __version__
 from poetry.config.config import Config
+from poetry.console.exceptions import ConsoleMessage
+from poetry.console.exceptions import PoetryRuntimeError
 from poetry.exceptions import PoetryError
 from poetry.utils.constants import REQUESTS_TIMEOUT
 from poetry.utils.constants import RETRY_AFTER_HEADER
@@ -230,7 +232,28 @@ def request(
                 resp = session.send(prepared_request, **send_kwargs)
             except (requests.exceptions.ConnectionError, OSError) as e:
                 if is_last_attempt:
-                    raise e
+                    parsed_url = urllib.parse.urlsplit(url)
+                    exc = PoetryRuntimeError.create(
+                        reason=f"<error>All attempts to connect to <c1>{parsed_url.netloc}</> failed.</>",
+                        exception=e,
+                    )
+                    exc.append(
+                        ConsoleMessage(
+                            "the server is not responding to requests at the moment\n"
+                            "the hostname cannot be resolved by your DNS\n"
+                            "your network is not connected to the internet\n"
+                        )
+                        .indent("    - ")
+                        .make_section("Probable Causes")
+                        .wrap("warning")
+                    )
+                    exc.append(
+                        ConsoleMessage(
+                            f"<b>Note:</> The path requested was <c1>{parsed_url.path}</>.",
+                            debug=True,
+                        )
+                    )
+                    raise exc
             else:
                 if resp.status_code not in STATUS_FORCELIST or is_last_attempt:
                     if raise_for_status:
@@ -245,7 +268,7 @@ def request(
                 continue
 
         # this should never really be hit under any sane circumstance
-        raise PoetryError("Failed HTTP {} request", method.upper())
+        raise PoetryError(f"Failed HTTP request: {method.upper()} {url}")
 
     def _get_backoff(self, response: requests.Response | None, attempt: int) -> float:
         if response is not None:
diff --git a/tests/console/test_exections_poetry_runtime_error.py b/tests/console/test_exections_poetry_runtime_error.py
index db687c1f43b..e2acb93dfb3 100644
--- a/tests/console/test_exections_poetry_runtime_error.py
+++ b/tests/console/test_exections_poetry_runtime_error.py
@@ -139,3 +139,10 @@ def test_poetry_runtime_error_create(
 
     actual_texts = [msg.text for msg in error._messages]
     assert actual_texts == expected_message_texts
+
+
+def test_poetry_runtime_error_append() -> None:
+    """Test the append method of PoetryRuntimeError."""
+    error = PoetryRuntimeError.create("Error", info=["Hello"]).append("World")
+    actual_texts = [msg.text for msg in error._messages]
+    assert actual_texts == ["Error", "<info>Hello</>", "World"]
diff --git a/tests/utils/test_authenticator.py b/tests/utils/test_authenticator.py
index 9bdc6eed55d..7644af20fb3 100644
--- a/tests/utils/test_authenticator.py
+++ b/tests/utils/test_authenticator.py
@@ -16,6 +16,7 @@
 from cleo.io.null_io import NullIO
 from keyring.credentials import SimpleCredential
 
+from poetry.console.exceptions import PoetryRuntimeError
 from poetry.utils.authenticator import Authenticator
 from poetry.utils.authenticator import RepositoryCertificateConfig
 from poetry.utils.password_manager import PoetryKeyring
@@ -279,9 +280,10 @@ def callback(*_: Any, **___: Any) -> None:
     http.register_uri(httpretty.GET, sdist_uri, body=callback)
     authenticator = Authenticator(config, NullIO())
 
-    with pytest.raises(requests.exceptions.ConnectionError):
+    with pytest.raises(PoetryRuntimeError) as e:
         authenticator.request("get", sdist_uri)
 
+    assert str(e.value) == "All attempts to connect to foo.bar failed."
     assert sleep.call_count == 5