diff --git a/lib/kamal/secrets/dotenv/inline_command_substitution.rb b/lib/kamal/secrets/dotenv/inline_command_substitution.rb
index c9ef98799..bc4f05508 100644
--- a/lib/kamal/secrets/dotenv/inline_command_substitution.rb
+++ b/lib/kamal/secrets/dotenv/inline_command_substitution.rb
@@ -4,9 +4,36 @@ def install!
       ::Dotenv::Parser.substitutions.map! { |sub| sub == ::Dotenv::Substitutions::Command ? self : sub }
     end
 
+    # Improved version of Dotenv::Substitutions::Command's INTERPOLATED_SHELL_COMMAND
+    # Handles:
+    #   $(echo 'foo)')
+    #   $(echo "foo)")
+    #   $(echo foo\))
+    #   $(echo "foo\")")
+    #   $(echo foo\\)
+    #   $(echo 'foo'"'"')')
+    INTERPOLATED_SHELL_COMMAND = /
+      (?<backslash>\\)?         # (1) Optional backslash (escaped '$')
+      \$                        # (2) Match a literal '$' (start of command)
+      (?<cmd>                   # (3) Capture the command within '$()' as 'cmd'
+        \(                      # (4) Require an opening parenthesis '('
+        (?:                     # (5) Match either:
+          [^()\\'"]+            #     - Any non-parens, non-escape, non-quotes (normal chars)
+          | \\ (?!\)) .         #     - Escaped character (e.g., `\(`, `\'`, `\"`), but **not** `\)` alone
+          | \\\\ \)             #     - Special case: Match `\\)` as a literal `\)`
+          | '(?:[^'\\]* (?:\\.[^'\\]*)*)'  # - Single-quoted strings with escaped quotes (`\'`)
+          | "(?:[^"\\]* (?:\\.[^"\\]*)*)"  # - Double-quoted strings with escaped quotes (`\"`)
+          | '(?:[^']*)' (?:"[^"]*")*       # - Single-quoted, followed by optional mixed double-quoted parts
+          | "(?:[^"]*)" (?:'[^']*')*       # - Double-quoted, followed by optional mixed single-quoted parts
+          | \g<cmd>             #     - Nested `$()` expressions (recursive call)
+        )*                      # (6) Repeat to allow full parsing
+        \)                      # (7) Require a closing parenthesis ')'
+      )
+    /x
+
     def call(value, _env, overwrite: false)
       # Process interpolated shell commands
-      value.gsub(Dotenv::Substitutions::Command.singleton_class::INTERPOLATED_SHELL_COMMAND) do |*|
+      value.gsub(INTERPOLATED_SHELL_COMMAND) do |*|
         # Eliminate opening and closing parentheses
         command = $LAST_MATCH_INFO[:cmd][1..-2]
 
diff --git a/test/secrets_test.rb b/test/secrets_test.rb
index f0ca7e299..9d0bed9c3 100644
--- a/test/secrets_test.rb
+++ b/test/secrets_test.rb
@@ -34,6 +34,30 @@ class SecretsTest < ActiveSupport::TestCase
     end
   end
 
+  test "secret with open bracket" do
+    with_test_secrets("secrets" => "SECRET1=$(echo 'foo)')") do
+      assert_equal "foo)", Kamal::Secrets.new["SECRET1"]
+    end
+  end
+
+  test "secret with close bracket" do
+    with_test_secrets("secrets" => "SECRET1=$(echo 'foo(')") do
+      assert_equal "foo(", Kamal::Secrets.new["SECRET1"]
+    end
+  end
+
+  test "secret with escaped quote" do
+    with_test_secrets("secrets" => "SECRET1=$(echo \"foo\\\")") do
+      assert_equal "foo", Kamal::Secrets.new["SECRET1"]
+    end
+  end
+
+  test "secret with escaped single quote" do
+    with_test_secrets("secrets" => "SECRET1=  $(echo 'foo'\"'\"'bar')") do
+      assert_equal "foo'bar", Kamal::Secrets.new["SECRET1"]
+    end
+  end
+
   test "destinations" do
     with_test_secrets("secrets.dest" => "SECRET=DEF", "secrets" => "SECRET=ABC", "secrets-common" => "SECRET=GHI\nSECRET2=JKL") do
       assert_equal "ABC", Kamal::Secrets.new["SECRET"]