diff --git a/src/coverage_reporter/api.cr b/src/coverage_reporter/api.cr
index 663642dd..2e785e65 100644
--- a/src/coverage_reporter/api.cr
+++ b/src/coverage_reporter/api.cr
@@ -52,6 +52,19 @@ module CoverageReporter
       OpenSSL::SSL::Context::Client.insecure
     end
 
+    def with_ssl_errors_handling() : HTTP::Client::Response
+      begin
+        yield
+      rescue ex
+        if OpenSSLVersion.new.can_fail?
+          Log.error <<-ERROR
+            Consider upgrading `openssl` library to version >= #{OpenSSLVersion::WORKS} or using --force-insecure-requests flag
+          ERROR
+        end
+        raise(ex)
+      end
+    end
+
     def with_redirects(uri : URI, max_redirects : Int32 = 10, & : URI -> HTTP::Client::Response) : HTTP::Client::Response
       redirect_num = 0
       response = yield(uri)
diff --git a/src/coverage_reporter/api/jobs.cr b/src/coverage_reporter/api/jobs.cr
index a9ff8a42..d0e0b11d 100644
--- a/src/coverage_reporter/api/jobs.cr
+++ b/src/coverage_reporter/api/jobs.cr
@@ -64,12 +64,14 @@ module CoverageReporter
         headers.merge!(HTTP::Headers{"Content-Type" => content_type.gsub("\"", "")})
 
         response = Api.with_redirects(jobs_uri) do |uri|
-          HTTP::Client.post(
-            uri,
-            body: body,
-            headers: headers,
-            tls: Api.tls_for(uri, @config.force_insecure_requests)
-          )
+          Api.with_ssl_errors_handling do
+            HTTP::Client.post(
+              uri,
+              body: body,
+              headers: headers,
+              tls: Api.tls_for(uri, @config.force_insecure_requests)
+            )
+          end
         end
 
         Api.handle_response(response)
diff --git a/src/coverage_reporter/api/webhook.cr b/src/coverage_reporter/api/webhook.cr
index 82547441..0048d752 100644
--- a/src/coverage_reporter/api/webhook.cr
+++ b/src/coverage_reporter/api/webhook.cr
@@ -35,12 +35,14 @@ module CoverageReporter
       })
 
       res = Api.with_redirects(webhook_uri) do |uri|
-        HTTP::Client.post(
-          uri,
-          headers: headers,
-          body: data.to_json,
-          tls: Api.tls_for(uri, @config.force_insecure_requests)
-        )
+        Api.with_ssl_errors_handling do
+          HTTP::Client.post(
+            uri,
+            headers: headers,
+            body: data.to_json,
+            tls: Api.tls_for(uri, @config.force_insecure_requests)
+          )
+        end
       end
 
       Api.handle_response(res)