diff --git a/.changesets/warn-about-deprecated-working_dir_path-option-from-all-config-sources.md b/.changesets/warn-about-deprecated-working_dir_path-option-from-all-config-sources.md
new file mode 100644
index 000000000..5a1978885
--- /dev/null
+++ b/.changesets/warn-about-deprecated-working_dir_path-option-from-all-config-sources.md
@@ -0,0 +1,6 @@
+---
+bump: "patch"
+type: "deprecate"
+---
+
+Warn about the deprecated `working_dir_path` option from all config sources. It previously only printed a warning when it was configured in the `config/appsignal.yml` file, but now also prints the warning if it's set via the Config class initialize options and environment variables. Please use the `working_directory_path` option instead.
diff --git a/lib/appsignal/config.rb b/lib/appsignal/config.rb
index c669f157a..7b6be65d4 100644
--- a/lib/appsignal/config.rb
+++ b/lib/appsignal/config.rb
@@ -377,12 +377,9 @@ def load_from_disk
       configurations = YAML.load(ERB.new(IO.read(config_file)).result, **read_options)
       config_for_this_env = configurations[env]
       if config_for_this_env
-        config_for_this_env =
-          config_for_this_env.each_with_object({}) do |(key, value), hash|
-            hash[key.to_sym] = value # convert keys to symbols
-          end
-
-        maintain_file_config_backwards_compatibility(config_for_this_env)
+        config_for_this_env.each_with_object({}) do |(key, value), hash|
+          hash[key.to_sym] = value # convert keys to symbols
+        end
       else
         logger.error "Not loading from config file: config for '#{env}' not found"
         nil
@@ -397,26 +394,6 @@ def load_from_disk
       nil
     end
 
-    # Maintain backwards compatibility with config files generated by earlier
-    # versions of the gem
-    #
-    # Used by {#load_from_disk}. No compatibility for env variables or initial config currently.
-    #
-    # @todo This is incomplete and only considers the file source as the only
-    #   valid config source. This should be moved to
-    #   {maintain_backwards_compatibility}.
-    def maintain_file_config_backwards_compatibility(configuration)
-      configuration.tap do |config|
-        if config.include?(:working_dir_path)
-          deprecation_message \
-            "'working_dir_path' is deprecated, please use " \
-            "'working_directory_path' instead and specify the " \
-            "full path to the working directory",
-            logger
-        end
-      end
-    end
-
     # Maintain backwards compatibility with deprecated config options.
     #
     # Add deprecated config options here with the behavior of setting its
@@ -442,6 +419,14 @@ def maintain_backwards_compatibility
           "deprecated. Please use `send_session_data` instead.",
           logger
       end
+
+      if config_hash.key?(:working_dir_path) # rubocop:disable Style/GuardClause
+        deprecation_message \
+          "The `working_dir_path` option is deprecated, please use " \
+          "`working_directory_path` instead and specify the " \
+          "full path to the working directory",
+          logger
+      end
     end
 
     def load_from_environment
diff --git a/spec/lib/appsignal/config_spec.rb b/spec/lib/appsignal/config_spec.rb
index 55af450ea..60f8727a4 100644
--- a/spec/lib/appsignal/config_spec.rb
+++ b/spec/lib/appsignal/config_spec.rb
@@ -751,6 +751,45 @@
       described_class.new(Dir.pwd, "production", config_options, logger)
     end
 
+    describe "working_dir_path" do
+      let(:err_stream) { std_stream }
+      let(:stderr) { err_stream.read }
+      let(:deprecation_message) do
+        "The `working_dir_path` option is deprecated, please use " \
+          "`working_directory_path` instead and specify the " \
+          "full path to the working directory"
+      end
+      before do
+        capture_std_streams(std_stream, err_stream) { config }
+      end
+
+      context "when not set" do
+        let(:config_options) { {} }
+
+        it "sets the default working_dir_path value" do
+          expect(config[:working_dir_path]).to be_nil
+        end
+
+        it "does not print a deprecation warning" do
+          expect(stderr).to_not include("appsignal WARNING: #{deprecation_message}")
+          expect(logs).to_not include(deprecation_message)
+        end
+      end
+
+      context "when set" do
+        let(:config_options) { { :working_dir_path => "/tmp/appsignal2" } }
+
+        it "sets the default working_dir_path value" do
+          expect(config[:working_dir_path]).to eq("/tmp/appsignal2")
+        end
+
+        it "does not print a deprecation warning" do
+          expect(stderr).to include("appsignal WARNING: #{deprecation_message}")
+          expect(logs).to include(deprecation_message)
+        end
+      end
+    end
+
     describe "skip_session_data" do
       let(:err_stream) { std_stream }
       let(:stderr) { err_stream.read }