diff --git a/test/v2_integration.py b/test/v2_integration.py
index e48842110..42eb026d3 100644
--- a/test/v2_integration.py
+++ b/test/v2_integration.py
@@ -63,6 +63,43 @@ def rand_http_chall(client):
                 return d, c.chall
     raise Exception("No HTTP-01 challenge found for random domain authz")
 
+def test_http_challenge_broken_redirect():
+    """
+    test_http_challenge_broken_redirect tests that a common webserver
+    mis-configuration receives the correct specialized error message when attempting
+    an HTTP-01 challenge.
+    """
+    client = chisel2.make_client()
+
+    # Create an authz for a random domain and get its HTTP-01 challenge token
+    d, chall = rand_http_chall(client)
+    token = chall.encode("token")
+
+    # Create a broken HTTP redirect similar to a sort we see frequently "in the wild"
+    challengePath = "/.well-known/acme-challenge/{0}".format(token)
+    redirect = "http://{0}.well-known/acme-challenge/bad-bad-bad".format(d)
+    challSrv.add_http_redirect(
+        challengePath,
+        redirect)
+
+    # Expect the specialized error message
+    expectedError = "Fetching {0}: Invalid host in redirect target \"{1}.well-known\". Check webserver config for missing '/' in redirect target.".format(redirect, d)
+
+    # NOTE(@cpu): Can't use chisel2.expect_problem here because it doesn't let
+    # us interrogate the detail message easily.
+    try:
+        chisel2.auth_and_issue([d], client=client, chall_type="http-01")
+    except acme_errors.ValidationError as e:
+        for authzr in e.failed_authzrs:
+            c = chisel2.get_chall(authzr, challenges.HTTP01)
+            error = c.error
+            if error is None or error.typ != "urn:ietf:params:acme:error:connection":
+                raise Exception("Expected connection prob, got %s" % (error.__str__()))
+            if error.detail != expectedError:
+                raise Exception("Expected prob detail %s, got %s" % (expectedError, error.detail))
+
+    challSrv.remove_http_redirect(challengePath)
+
 def test_http_challenge_loop_redirect():
     client = chisel2.make_client()
 
diff --git a/va/http.go b/va/http.go
index c2a96799e..3032374d3 100644
--- a/va/http.go
+++ b/va/http.go
@@ -314,6 +314,22 @@ func (va *ValidationAuthorityImpl) extractRequestTarget(req *http.Request) (stri
 				"Only domain names are supported, not IP addresses", reqHost)
 	}
 
+	// Often folks will misconfigure their webserver to send an HTTP redirect
+	// missing a `/' between the FQDN and the path. E.g. in Apache using:
+	//   Redirect / https://bad-redirect.org
+	// Instead of
+	//   Redirect / https://bad-redirect.org/
+	// Will produce an invalid HTTP-01 redirect target like:
+	//   https://bad-redirect.org.well-known/acme-challenge/xxxx
+	// This happens frequently enough we want to return a distinct error message
+	// for this case by detecting the reqHost ending in ".well-known".
+	if strings.HasSuffix(reqHost, ".well-known") {
+		return "", 0, berrors.ConnectionFailureError(
+			"Invalid host in redirect target %q. Check webserver config for missing '/' in redirect target.",
+			reqHost,
+		)
+	}
+
 	if _, err := iana.ExtractSuffix(reqHost); err != nil {
 		return "", 0, berrors.ConnectionFailureError(
 			"Invalid hostname in redirect target, must end in IANA registered TLD")
diff --git a/va/http_test.go b/va/http_test.go
index 18780b695..ce2165451 100644
--- a/va/http_test.go
+++ b/va/http_test.go
@@ -232,6 +232,13 @@ func TestExtractRequestTarget(t *testing.T) {
 			},
 			ExpectedError: errors.New("Invalid empty hostname in redirect target"),
 		},
+		{
+			Name: "invalid .well-known hostname",
+			Req: &http.Request{
+				URL: mustURL(t, "https://my.webserver.is.misconfigured.well-known/acme-challenge/xxx"),
+			},
+			ExpectedError: errors.New(`Invalid host in redirect target "my.webserver.is.misconfigured.well-known". Check webserver config for missing '/' in redirect target.`),
+		},
 		{
 			Name: "invalid non-iana hostname",
 			Req: &http.Request{