diff --git a/Library/Homebrew/cask/upgrade.rb b/Library/Homebrew/cask/upgrade.rb
index 54e76880c6cac..4da2ec4a58096 100644
--- a/Library/Homebrew/cask/upgrade.rb
+++ b/Library/Homebrew/cask/upgrade.rb
@@ -40,8 +40,6 @@ def self.upgrade_casks(
 
       quarantine = true if quarantine.nil?
 
-      greedy = true if Homebrew::EnvConfig.upgrade_greedy?
-
       outdated_casks = if casks.empty?
         Caskroom.casks(config: Config.from_args(args)).select do |cask|
           cask.outdated?(greedy: greedy, greedy_latest: greedy_latest,
diff --git a/Library/Homebrew/cmd/outdated.rb b/Library/Homebrew/cmd/outdated.rb
index 6df2c6e2d2553..95dd306c1ce7d 100644
--- a/Library/Homebrew/cmd/outdated.rb
+++ b/Library/Homebrew/cmd/outdated.rb
@@ -32,13 +32,16 @@ def self.outdated_args
                           "formula is outdated. Otherwise, the repository's HEAD will only be checked for " \
                           "updates when a new stable or development version has been released."
       switch "-g", "--greedy",
-             description: "Also include outdated casks with `auto_updates true` or `version :latest`."
+             description: "Also include outdated casks with `auto_updates true` or `version :latest`.",
+             env:         :cask_upgrade_greedy
 
       switch "--greedy-latest",
-             description: "Also include outdated casks including those with `version :latest`."
+             description: "Also include outdated casks including those with `version :latest`.",
+             env:         :cask_upgrade_greedy_latest
 
       switch "--greedy-auto-updates",
-             description: "Also include outdated casks including those with `auto_updates true`."
+             description: "Also include outdated casks including those with `auto_updates true`.",
+             env:         :cask_upgrade_greedy_auto_updates
 
       conflicts "--quiet", "--verbose", "--json"
       conflicts "--formula", "--cask"
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index ed712f3070f24..01956566eb314 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -91,12 +91,15 @@ def upgrade_args
         }],
         [:switch, "-g", "--greedy", {
           description: "Also include casks with `auto_updates true` or `version :latest`.",
+          env:         :cask_upgrade_greedy,
         }],
         [:switch, "--greedy-latest", {
           description: "Also include casks with `version :latest`.",
+          env:         :cask_upgrade_greedy_latest,
         }],
         [:switch, "--greedy-auto-updates", {
           description: "Also include casks with `auto_updates true`.",
+          env:         :cask_upgrade_greedy_auto_updates,
         }],
         [:switch, "--[no-]binaries", {
           description: "Disable/enable linking of helper executables (default: enabled).",
diff --git a/Library/Homebrew/env_config.rb b/Library/Homebrew/env_config.rb
index c5d04c4082bad..ce5decaa09830 100644
--- a/Library/Homebrew/env_config.rb
+++ b/Library/Homebrew/env_config.rb
@@ -341,8 +341,9 @@ module EnvConfig
         boolean:     true,
       },
       HOMEBREW_UPGRADE_GREEDY:                   {
-        description: "If set, pass `--greedy` to all cask upgrade commands.",
-        boolean:     true,
+        description: "When set to \"auto-updates\", \"latest\", or any other value (e.g. \"1\"), pass " \
+                     "`--greedy-auto-updates`, `--greedy-latest`, or `--greedy` respectively to all cask " \
+                     "upgrade commands.",
       },
       HOMEBREW_SIMULATE_MACOS_ON_LINUX:          {
         description: "If set, running Homebrew on Linux will simulate certain macOS code paths. This is useful " \
@@ -504,5 +505,22 @@ def cask_opts_require_sha?
     def automatically_set_no_install_from_api?
       ENV["HOMEBREW_AUTOMATICALLY_SET_NO_INSTALL_FROM_API"].present?
     end
+
+    sig { returns(T::Boolean) }
+    def cask_upgrade_greedy?
+      ENV["HOMEBREW_UPGRADE_GREEDY"].present? &&
+        !cask_upgrade_greedy_latest? &&
+        !cask_upgrade_greedy_auto_updates?
+    end
+
+    sig { returns(T::Boolean) }
+    def cask_upgrade_greedy_latest?
+      ENV["HOMEBREW_UPGRADE_GREEDY"] == "latest"
+    end
+
+    sig { returns(T::Boolean) }
+    def cask_upgrade_greedy_auto_updates?
+      ENV["HOMEBREW_UPGRADE_GREEDY"] == "auto-updates"
+    end
   end
 end
diff --git a/Library/Homebrew/env_config.rbi b/Library/Homebrew/env_config.rbi
index 1fa98249b3404..91bc33bb2fdcd 100644
--- a/Library/Homebrew/env_config.rbi
+++ b/Library/Homebrew/env_config.rbi
@@ -232,8 +232,8 @@ module Homebrew::EnvConfig
   sig { returns(T::Boolean) }
   def self.update_to_tag?; end
 
-  sig { returns(T::Boolean) }
-  def self.upgrade_greedy?; end
+  sig { returns(T.nilable(String)) }
+  def self.upgrade_greedy; end
 
   sig { returns(T::Boolean) }
   def self.verbose?; end
diff --git a/Library/Homebrew/test/env_config_spec.rb b/Library/Homebrew/test/env_config_spec.rb
index 02fdd05948c89..b780b401d96d0 100644
--- a/Library/Homebrew/test/env_config_spec.rb
+++ b/Library/Homebrew/test/env_config_spec.rb
@@ -63,4 +63,85 @@
       expect(env_config.make_jobs).to eql("16")
     end
   end
+
+  describe ".cask_upgrade_greedy" do
+    it "returns true if \"HOMEBREW_UPGRADE_GREEDY\" set to \"1\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "1"
+      expect(env_config.cask_upgrade_greedy?).to be(true)
+    end
+
+    it "returns true if \"HOMEBREW_UPGRADE_GREEDY\" set to \"true\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "true"
+      expect(env_config.cask_upgrade_greedy?).to be(true)
+    end
+
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"latest\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "latest"
+      expect(env_config.cask_upgrade_greedy?).to be(false)
+    end
+
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"auto-updates\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "auto-updates"
+      expect(env_config.cask_upgrade_greedy?).to be(false)
+    end
+
+    it "returns false by default" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = ""
+      expect(env_config.cask_upgrade_greedy?).to be(false)
+    end
+  end
+
+  describe ".cask_upgrade_greedy_latest" do
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"1\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "1"
+      expect(env_config.cask_upgrade_greedy_latest?).to be(false)
+    end
+
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"true\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "true"
+      expect(env_config.cask_upgrade_greedy_latest?).to be(false)
+    end
+
+    it "returns true if \"HOMEBREW_UPGRADE_GREEDY\" set to \"latest\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "latest"
+      expect(env_config.cask_upgrade_greedy_latest?).to be(true)
+    end
+
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"auto-updates\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "auto-updates"
+      expect(env_config.cask_upgrade_greedy_latest?).to be(false)
+    end
+
+    it "returns false by default" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = ""
+      expect(env_config.cask_upgrade_greedy_latest?).to be(false)
+    end
+  end
+
+  describe ".cask_upgrade_greedy_auto_updates" do
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"1\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "1"
+      expect(env_config.cask_upgrade_greedy_auto_updates?).to be(false)
+    end
+
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"true\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "true"
+      expect(env_config.cask_upgrade_greedy_auto_updates?).to be(false)
+    end
+
+    it "returns false if \"HOMEBREW_UPGRADE_GREEDY\" set to \"latest\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "latest"
+      expect(env_config.cask_upgrade_greedy_auto_updates?).to be(false)
+    end
+
+    it "returns true if \"HOMEBREW_UPGRADE_GREEDY\" set to \"auto-updates\"" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = "auto-updates"
+      expect(env_config.cask_upgrade_greedy_auto_updates?).to be(true)
+    end
+
+    it "returns false by default" do
+      ENV["HOMEBREW_UPGRADE_GREEDY"] = ""
+      expect(env_config.cask_upgrade_greedy_auto_updates?).to be(false)
+    end
+  end
 end
diff --git a/docs/Manpage.md b/docs/Manpage.md
index 2abe611ece4b5..00801749302c0 100644
--- a/docs/Manpage.md
+++ b/docs/Manpage.md
@@ -2357,7 +2357,7 @@ command execution e.g. `$(cat file)`.
   <br>If set, use Pry for the `brew irb` command.
 
 - `HOMEBREW_UPGRADE_GREEDY`
-  <br>If set, pass `--greedy` to all cask upgrade commands.
+  <br>When set to "auto-updates", "latest", or any other value (e.g. "1"), pass `--greedy-auto-updates`, `--greedy-latest`, or `--greedy` respectively to all cask upgrade commands.
 
 - `HOMEBREW_SIMULATE_MACOS_ON_LINUX`
   <br>If set, running Homebrew on Linux will simulate certain macOS code paths. This is useful when auditing macOS formulae while on Linux.
diff --git a/manpages/brew.1 b/manpages/brew.1
index 69941c531d2f6..81468437be9d2 100644
--- a/manpages/brew.1
+++ b/manpages/brew.1
@@ -3464,7 +3464,7 @@ If set, use Pry for the \fBbrew irb\fR command\.
 \fBHOMEBREW_UPGRADE_GREEDY\fR
 .
 .br
-If set, pass \fB\-\-greedy\fR to all cask upgrade commands\.
+When set to "auto\-updates", "latest", or any other value (e\.g\. "1"), pass \fB\-\-greedy\-auto\-updates\fR, \fB\-\-greedy\-latest\fR, or \fB\-\-greedy\fR respectively to all cask upgrade commands\.
 .
 .TP
 \fBHOMEBREW_SIMULATE_MACOS_ON_LINUX\fR