diff --git a/enterprise/coderd/proxyhealth/proxyhealth.go b/enterprise/coderd/proxyhealth/proxyhealth.go
index 4b9e3f13982f8..9f3abdac849f2 100644
--- a/enterprise/coderd/proxyhealth/proxyhealth.go
+++ b/enterprise/coderd/proxyhealth/proxyhealth.go
@@ -289,7 +289,27 @@ func (p *ProxyHealth) runOnce(ctx context.Context, now time.Time) (map[uuid.UUID
 			case err == nil && resp.StatusCode != http.StatusOK:
 				// Unhealthy as we did reach the proxy but it got an unexpected response.
 				status.Status = Unhealthy
-				status.Report.Errors = []string{fmt.Sprintf("unexpected status code %d", resp.StatusCode)}
+				var builder strings.Builder
+				// This string is shown on the UI where newlines are respected.
+				// This error message is not ever decoded programmatically, so keep it human-
+				// readable.
+				builder.WriteString(fmt.Sprintf("unexpected status code %d. ", resp.StatusCode))
+				builder.WriteString(fmt.Sprintf("\nEncountered error, send a request to %q from the Coderd environment to debug this issue.", reqURL))
+				err := codersdk.ReadBodyAsError(resp)
+				if err != nil {
+					var apiErr *codersdk.Error
+					if xerrors.As(err, &apiErr) {
+						builder.WriteString(fmt.Sprintf("\nError Message: %s\nError Detail: %s", apiErr.Message, apiErr.Detail))
+						for _, v := range apiErr.Validations {
+							// Pretty sure this is not possible from the called endpoint, but just in case.
+							builder.WriteString(fmt.Sprintf("\n\tValidation: %s=%s", v.Field, v.Detail))
+						}
+					} else {
+						builder.WriteString(fmt.Sprintf("\nError: %s", err.Error()))
+					}
+				}
+
+				status.Report.Errors = []string{builder.String()}
 			case err != nil:
 				// Request failed, mark the proxy as unreachable.
 				status.Status = Unreachable