diff --git a/.config/rubocop/config.yml b/.config/rubocop/config.yml
index bb2750e..39b33dd 100644
--- a/.config/rubocop/config.yml
+++ b/.config/rubocop/config.yml
@@ -1,2 +1,6 @@
 inherit_gem:
   caliber: config/all.yml
+
+Metrics/ParameterLists:
+  Exclude:
+    - lib/trmnl/api/requester.rb
diff --git a/.reek.yml b/.reek.yml
index a2736e3..bc20f04 100644
--- a/.reek.yml
+++ b/.reek.yml
@@ -3,5 +3,11 @@ exclude_paths:
   - vendor
 
 detectors:
+  DataClump:
+    exclude:
+      - TRMNL::API::Requester
   LongParameterList:
     enabled: false
+  TooManyStatements:
+    exclude:
+      - TRMNL::API::Requester#call
diff --git a/lib/trmnl/api/requester.rb b/lib/trmnl/api/requester.rb
index 950a519..62f32ce 100644
--- a/lib/trmnl/api/requester.rb
+++ b/lib/trmnl/api/requester.rb
@@ -6,9 +6,8 @@ require "http"
 module TRMNL
   module API
     # Provides a low level configurable and monadic API client.
-    # :reek:DataClump
     class Requester
-      include Dependencies[:settings, :http]
+      include Dependencies[:settings, :http, :logger]
       include Dry::Monads[:result]
 
       HEADERS = {}.freeze
@@ -26,13 +25,32 @@ module TRMNL
 
       attr_reader :settings, :http
 
-      # rubocop:todo Metrics/ParameterLists
       def call method, path, headers, **options
         http.headers(settings.headers.merge(headers))
-            .public_send(method, "#{settings.uri}/#{path}", options)
+            .public_send(method, uri(path), options)
             .then { |response| response.status.success? ? Success(response) : Failure(response) }
+      rescue HTTP::ConnectionError => error then handle_bad_connection path, error
+      rescue HTTP::TimeoutError => error then handle_timeout path, error
+      rescue OpenSSL::SSL::SSLError => error then handle_bad_ssl path, error
+      end
+
+      def uri(path) = "#{settings.uri}/#{path}"
+
+      def handle_bad_connection path, error
+        logger.debug { error.message }
+        Failure "Unable to connect: #{uri(path).inspect}. Is the network intermittent or down?"
+      end
+
+      def handle_timeout path, error
+        logger.debug { error.message }
+        Failure "Connection timed out: #{uri(path).inspect}."
+      end
+
+      def handle_bad_ssl path, error
+        logger.debug { error.message }
+        Failure "Unable to secure connection: #{uri(path).inspect}. " \
+                "Is your certificate or SSL valid?"
       end
-      # rubocop:enable Metrics/ParameterLists
     end
   end
 end
diff --git a/spec/lib/trmnl/api/requester_spec.rb b/spec/lib/trmnl/api/requester_spec.rb
index dc953ea..41dc97e 100644
--- a/spec/lib/trmnl/api/requester_spec.rb
+++ b/spec/lib/trmnl/api/requester_spec.rb
@@ -69,7 +69,7 @@ RSpec.describe TRMNL::API::Requester do
       end
     end
 
-    context "with failure" do
+    context "with HTTP error status" do
       let :http do
         HTTP::Fake::Client.new do
           get "/api/current_screen" do
@@ -85,13 +85,72 @@ RSpec.describe TRMNL::API::Requester do
         end
       end
 
-      it "answers failure response" do
+      it "answers failure" do
         response = requester.get "current_screen"
         payload = response.alt_map { |result| result.parse.symbolize_keys! }
 
         expect(payload).to be_failure(message: "Danger!")
       end
     end
+
+    context "with connection failure" do
+      let :http do
+        class_spy(HTTP).tap do |spy|
+          allow(spy).to receive(:headers).and_raise HTTP::ConnectionError, "Danger!"
+        end
+      end
+
+      it "logs debug message" do
+        requester.get "current_screen"
+        expect(logger.reread).to match(/🔎.+Danger!/)
+      end
+
+      it "answers failure" do
+        expect(requester.get("current_screen")).to be_failure(
+          %(Unable to connect: "https://trmnl.app/api/current_screen". ) \
+          "Is the network intermittent or down?"
+        )
+      end
+    end
+
+    context "with timeout failure" do
+      let :http do
+        class_spy(HTTP).tap do |spy|
+          allow(spy).to receive(:headers).and_raise HTTP::TimeoutError, "Danger!"
+        end
+      end
+
+      it "logs debug message" do
+        requester.get "current_screen"
+        expect(logger.reread).to match(/🔎.+Danger!/)
+      end
+
+      it "answers failure" do
+        expect(requester.get("current_screen")).to be_failure(
+          %(Connection timed out: "https://trmnl.app/api/current_screen".)
+        )
+      end
+    end
+
+    context "with SSL failure" do
+      let :http do
+        class_spy(HTTP).tap do |spy|
+          allow(spy).to receive(:headers).and_raise OpenSSL::SSL::SSLError, "Danger!"
+        end
+      end
+
+      it "logs debug message" do
+        requester.get "current_screen"
+        expect(logger.reread).to match(/🔎.+Danger!/)
+      end
+
+      it "answers failure" do
+        expect(requester.get("current_screen")).to be_failure(
+          %(Unable to secure connection: "https://trmnl.app/api/current_screen". ) \
+          "Is your certificate or SSL valid?"
+        )
+      end
+    end
   end
 
   describe "#post" do