diff --git a/spec/acceptance/non_meterpreter_spec.rb b/spec/acceptance/non_meterpreter_spec.rb
index 46385353a0724..02fc79c485053 100644
--- a/spec/acceptance/non_meterpreter_spec.rb
+++ b/spec/acceptance/non_meterpreter_spec.rb
@@ -141,17 +141,18 @@ def initialize(path)
             session_id = nil
 
             # Wait for the session to open, or break early if the payload is detected as dead
-            wait_for_expect do
+            larger_retry_count_for_powershell = 600
+            wait_for_expect(larger_retry_count_for_powershell) do
               unless payload_process.alive?
                 break
               end
 
               # TODO: Was strictly for Meterpreter sessions, now more generic
               #   - can be reverted if we decide to move these new tests
-              session_opened_matcher = /\w.* session (\d+) opened[^\n]*\n/
+              session_opened_matcher = /session (\d+) opened[^\n]*\n/
               session_message = ''
               begin
-                session_message = console.recvuntil(session_opened_matcher, timeout: 1)
+                session_message = console.recvuntil_debug(session_opened_matcher, timeout: 1)
               rescue Acceptance::ChildProcessRecvError
                 # noop
               end
diff --git a/spec/support/acceptance/child_process.rb b/spec/support/acceptance/child_process.rb
index cb70f50f3043e..fc07b8e3c08b0 100644
--- a/spec/support/acceptance/child_process.rb
+++ b/spec/support/acceptance/child_process.rb
@@ -101,6 +101,42 @@ def recvuntil(delim, timeout: @default_timeout, drop_delim: false)
       raise ChildProcessRecvError, "Failed #{__method__}: Did not match #{delim.inspect}, process was alive?=#{alive?.inspect}, remaining buffer: #{self.buffer.string[self.buffer.pos..].inspect}"
     end
 
+
+    def recvuntil_debug(delim, timeout: @default_timeout, drop_delim: false)
+      buffer = ''
+      result = nil
+
+      with_countdown(timeout) do |countdown|
+        while alive? && !countdown.elapsed?
+          data_chunk = recv(timeout: [countdown.remaining_time, 1].min)
+          if !data_chunk
+            next
+          end
+
+          buffer += data_chunk
+          $stderr.puts "Attempting o to match buffer: #{buffer.inspect} with delim #{delim.inspect}"
+          has_delimiter = delim.is_a?(Regexp) ? buffer.match?(delim) : buffer.include?(delim)
+          next unless has_delimiter
+
+          result, matched_delim, remaining = buffer.partition(delim)
+          unless drop_delim
+            result += matched_delim
+          end
+          unrecv(remaining)
+          # Reset the temporary buffer to avoid the `ensure` mechanism unrecv'ing the buffer unintentionally
+          buffer = ''
+
+          return result
+        end
+      ensure
+        unrecv(buffer)
+      end
+
+      result
+    rescue ChildProcessTimeoutError
+      raise ChildProcessRecvError, "Failed #{__method__}: Did not match #{delim.inspect}, process was alive?=#{alive?.inspect}, remaining buffer: #{self.buffer.string[self.buffer.pos..].inspect}"
+    end
+
     # @return [String] Recv until additional reads would cause a block, or eof is reached, or a maximum timeout is reached
     def recv_available(timeout: @default_timeout)
       result = ''