diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1380268e26..6749707345 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -40,7 +40,8 @@
 - [#8690](https://github.com/influxdata/influxdb/issues/8690): Implicitly decide on a lower limit for fill queries when none is present.
 - [#8947](https://github.com/influxdata/influxdb/pull/8947): Add `EXPLAIN ANALYZE` command, which produces a detailed execution plan of a `SELECT` statement.
 - [#8963](https://github.com/influxdata/influxdb/pull/8963): Streaming inmem2tsi conversion.
-- [#8995](https://github.com/influxdata/influxdb/pull/8995): Sort & validate TSI key value insertion. 
+- [#8995](https://github.com/influxdata/influxdb/pull/8995): Sort & validate TSI key value insertion.
+- [#8968](https://github.com/influxdata/influxdb/issues/8968): Make client errors more helpful on downstream errs
 
 ### Bugfixes
 
@@ -153,7 +154,7 @@ The following new configuration options are available.
 * `max-body-size` was added with a default of 25,000,000, but can be disabled by setting it to 0.
   Specifies the maximum size (in bytes) of a client request body. When a client sends data that exceeds
   the configured maximum size, a `413 Request Entity Too Large` HTTP response is returned.
-  
+
 #### `[continuous_queries]` Section
 
 * `query-stats-enabled` was added with a default of `false`. When set to `true`, continuous query execution statistics are written to the default monitor store.
diff --git a/client/v2/client.go b/client/v2/client.go
index 7a057c13cd..2870cf8e50 100644
--- a/client/v2/client.go
+++ b/client/v2/client.go
@@ -9,6 +9,7 @@ import (
 	"fmt"
 	"io"
 	"io/ioutil"
+	"mime"
 	"net/http"
 	"net/url"
 	"strconv"
@@ -514,6 +515,31 @@ func (c *client) Query(q Query) (*Response, error) {
 	}
 	defer resp.Body.Close()
 
+	// If we lack a X-Influxdb-Version header, then we didn't get a response from influxdb
+	// but instead some other service. If the error code is also a 500+ code, then some
+	// downstream loadbalancer/proxy/etc had an issue and we should report that.
+	if resp.Header.Get("X-Influxdb-Version") == "" && resp.StatusCode >= http.StatusInternalServerError {
+		body, err := ioutil.ReadAll(resp.Body)
+		if err != nil || len(body) == 0 {
+			return nil, fmt.Errorf("received status code %d from downstream server", resp.StatusCode)
+		}
+
+		return nil, fmt.Errorf("received status code %d from downstream server, with response body: %q", resp.StatusCode, body)
+	}
+
+	// If we get an unexpected content type, then it is also not from influx direct and therefore
+	// we want to know what we received and what status code was returned for debugging purposes.
+	if cType, _, _ := mime.ParseMediaType(resp.Header.Get("Content-Type")); cType != "application/json" {
+		// Read up to 1kb of the body to help identify downstream errors and limit the impact of things
+		// like downstream serving a large file
+		body, err := ioutil.ReadAll(io.LimitReader(resp.Body, 1024))
+		if err != nil || len(body) == 0 {
+			return nil, fmt.Errorf("expected json response, got %q, with status: %v", cType, resp.StatusCode)
+		}
+
+		return nil, fmt.Errorf("expected json response, got %q, with status: %v and response body: %q", cType, resp.StatusCode, body)
+	}
+
 	var response Response
 	if q.Chunked {
 		cr := NewChunkedResponse(resp.Body)
@@ -548,11 +574,11 @@ func (c *client) Query(q Query) (*Response, error) {
 			return nil, fmt.Errorf("unable to decode json: received status code %d err: %s", resp.StatusCode, decErr)
 		}
 	}
+
 	// If we don't have an error in our json response, and didn't get statusOK
 	// then send back an error
 	if resp.StatusCode != http.StatusOK && response.Error() == nil {
-		return &response, fmt.Errorf("received status code %d from server",
-			resp.StatusCode)
+		return &response, fmt.Errorf("received status code %d from server", resp.StatusCode)
 	}
 	return &response, nil
 }
diff --git a/client/v2/client_test.go b/client/v2/client_test.go
index 5a0b092236..5edc866ef9 100644
--- a/client/v2/client_test.go
+++ b/client/v2/client_test.go
@@ -139,6 +139,7 @@ func (w *writeLogger) Close() error { return nil }
 func TestClient_Query(t *testing.T) {
 	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		var data Response
+		w.Header().Set("Content-Type", "application/json")
 		w.WriteHeader(http.StatusOK)
 		_ = json.NewEncoder(w).Encode(data)
 	}))
@@ -155,9 +156,126 @@ func TestClient_Query(t *testing.T) {
 	}
 }
 
+func TestClientDownstream500WithBody_Query(t *testing.T) {
+	const err500page = `<html>
+	<head>
+		<title>500 Internal Server Error</title>
+	</head>
+	<body>Internal Server Error</body>
+</html>`
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+		w.Write([]byte(err500page))
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{}
+	_, err := c.Query(query)
+
+	expected := fmt.Sprintf("received status code 500 from downstream server, with response body: %q", err500page)
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClientDownstream500_Query(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{}
+	_, err := c.Query(query)
+
+	expected := "received status code 500 from downstream server"
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClientDownstream400WithBody_Query(t *testing.T) {
+	const err403page = `<html>
+	<head>
+		<title>403 Forbidden</title>
+	</head>
+	<body>Forbidden</body>
+</html>`
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusForbidden)
+		w.Write([]byte(err403page))
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{}
+	_, err := c.Query(query)
+
+	expected := fmt.Sprintf(`expected json response, got "text/html", with status: %v and response body: %q`, http.StatusForbidden, err403page)
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClientDownstream400_Query(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusForbidden)
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{}
+	_, err := c.Query(query)
+
+	expected := fmt.Sprintf(`expected json response, got "text/plain", with status: %v`, http.StatusForbidden)
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClient500_Query(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		w.Header().Set("X-Influxdb-Version", "1.3.1")
+		w.WriteHeader(http.StatusInternalServerError)
+		w.Write([]byte(`{"error":"test"}`))
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{}
+	resp, err := c.Query(query)
+
+	if err != nil {
+		t.Errorf("unexpected error.  expected nothing, actual %v", err)
+	}
+
+	if resp.Err != "test" {
+		t.Errorf(`unexpected response error.  expected "test", actual %v`, resp.Err)
+	}
+}
+
 func TestClient_ChunkedQuery(t *testing.T) {
 	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		var data Response
+		w.Header().Set("Content-Type", "application/json")
+		w.Header().Set("X-Influxdb-Version", "1.3.1")
 		w.WriteHeader(http.StatusOK)
 		enc := json.NewEncoder(w)
 		_ = enc.Encode(data)
@@ -178,12 +296,130 @@ func TestClient_ChunkedQuery(t *testing.T) {
 	}
 }
 
+func TestClientDownstream500WithBody_ChunkedQuery(t *testing.T) {
+	const err500page = `<html>
+	<head>
+		<title>500 Internal Server Error</title>
+	</head>
+	<body>Internal Server Error</body>
+</html>`
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+		w.Write([]byte(err500page))
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, err := NewHTTPClient(config)
+	if err != nil {
+		t.Fatalf("unexpected error.  expected %v, actual %v", nil, err)
+	}
+
+	query := Query{Chunked: true}
+	_, err = c.Query(query)
+
+	expected := fmt.Sprintf("received status code 500 from downstream server, with response body: %q", err500page)
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClientDownstream500_ChunkedQuery(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{Chunked: true}
+	_, err := c.Query(query)
+
+	expected := "received status code 500 from downstream server"
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClient500_ChunkedQuery(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		w.Header().Set("X-Influxdb-Version", "1.3.1")
+		w.WriteHeader(http.StatusInternalServerError)
+		w.Write([]byte(`{"error":"test"}`))
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{Chunked: true}
+	resp, err := c.Query(query)
+
+	if err != nil {
+		t.Errorf("unexpected error.  expected nothing, actual %v", err)
+	}
+
+	if resp.Err != "test" {
+		t.Errorf(`unexpected response error.  expected "test", actual %v`, resp.Err)
+	}
+}
+
+func TestClientDownstream400WithBody_ChunkedQuery(t *testing.T) {
+	const err403page = `<html>
+	<head>
+		<title>403 Forbidden</title>
+	</head>
+	<body>Forbidden</body>
+</html>`
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusForbidden)
+		w.Write([]byte(err403page))
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{Chunked: true}
+	_, err := c.Query(query)
+
+	expected := fmt.Sprintf(`expected json response, got "text/html", with status: %v and response body: %q`, http.StatusForbidden, err403page)
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
+func TestClientDownstream400_ChunkedQuery(t *testing.T) {
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusForbidden)
+	}))
+	defer ts.Close()
+
+	config := HTTPConfig{Addr: ts.URL}
+	c, _ := NewHTTPClient(config)
+	defer c.Close()
+
+	query := Query{Chunked: true}
+	_, err := c.Query(query)
+
+	expected := fmt.Sprintf(`expected json response, got "text/plain", with status: %v`, http.StatusForbidden)
+	if err.Error() != expected {
+		t.Errorf("unexpected error.  expected %v, actual %v", expected, err)
+	}
+}
+
 func TestClient_BoundParameters(t *testing.T) {
 	var parameterString string
 	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		var data Response
 		r.ParseForm()
 		parameterString = r.FormValue("params")
+		w.Header().Set("Content-Type", "application/json")
 		w.WriteHeader(http.StatusOK)
 		_ = json.NewEncoder(w).Encode(data)
 	}))
@@ -233,6 +469,7 @@ func TestClient_BasicAuth(t *testing.T) {
 			t.Errorf("unexpected password, expected %q, actual %q", "password", p)
 		}
 		var data Response
+		w.Header().Set("Content-Type", "application/json")
 		w.WriteHeader(http.StatusOK)
 		_ = json.NewEncoder(w).Encode(data)
 	}))
@@ -252,6 +489,7 @@ func TestClient_BasicAuth(t *testing.T) {
 func TestClient_Ping(t *testing.T) {
 	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		var data Response
+		w.Header().Set("Content-Type", "application/json")
 		w.WriteHeader(http.StatusNoContent)
 		_ = json.NewEncoder(w).Encode(data)
 	}))
@@ -269,6 +507,7 @@ func TestClient_Ping(t *testing.T) {
 
 func TestClient_Concurrent_Use(t *testing.T) {
 	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
 		w.WriteHeader(http.StatusOK)
 		w.Write([]byte(`{}`))
 	}))
@@ -381,6 +620,7 @@ func TestClient_UserAgent(t *testing.T) {
 		receivedUserAgent = r.UserAgent()
 
 		var data Response
+		w.Header().Set("Content-Type", "application/json")
 		w.WriteHeader(http.StatusOK)
 		_ = json.NewEncoder(w).Encode(data)
 	}))
diff --git a/stress/stress_test.go b/stress/stress_test.go
index 6c1fa89513..94db4654b9 100644
--- a/stress/stress_test.go
+++ b/stress/stress_test.go
@@ -389,6 +389,7 @@ var basicQC = &BasicQueryClient{
 func TestBasicQueryClient_Query(t *testing.T) {
 	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		time.Sleep(50 * time.Millisecond)
+		w.Header().Set("Content-Type", "application/json; charset=utf-8")
 		w.Header().Set("X-Influxdb-Version", "x.x")
 		w.Header().Set("X-Influxdb-Build", "OSS")
 		var data client.Response