diff --git a/compiler.go b/compiler.go
index 311fd58423..547b9ac235 100644
--- a/compiler.go
+++ b/compiler.go
@@ -47,6 +47,19 @@ func (c *Compiler) FastGetVariables(t *ast.Task, call *Call) (*ast.Vars, error)
 func (c *Compiler) getVariables(t *ast.Task, call *Call, evaluateShVars bool) (*ast.Vars, error) {
 	result := env.GetEnviron()
 	specialVars, err := c.getSpecialVars(t, call)
+
+	if t != nil && t.Requires != nil {
+		for _, requiredVar := range t.Requires.Vars {
+			if requiredVar.Sh != "" {
+				newVar := ast.Var{
+					Sh: &requiredVar.Sh,
+				}
+				static, _ := c.HandleDynamicVar(newVar, c.Dir, env.GetFromVars(result))
+				requiredVar.Enum = strings.Split(static, "\n")
+			}
+		}
+	}
+
 	if err != nil {
 		return nil, err
 	}
diff --git a/taskfile/ast/requires.go b/taskfile/ast/requires.go
index 5a76e13fcd..2278a1356c 100644
--- a/taskfile/ast/requires.go
+++ b/taskfile/ast/requires.go
@@ -25,6 +25,7 @@ func (r *Requires) DeepCopy() *Requires {
 type VarsWithValidation struct {
 	Name string
 	Enum []string
+	Sh   string
 }
 
 func (v *VarsWithValidation) DeepCopy() *VarsWithValidation {
@@ -34,6 +35,7 @@ func (v *VarsWithValidation) DeepCopy() *VarsWithValidation {
 	return &VarsWithValidation{
 		Name: v.Name,
 		Enum: v.Enum,
+		Sh:   v.Sh,
 	}
 }
 
@@ -53,6 +55,7 @@ func (v *VarsWithValidation) UnmarshalYAML(node *yaml.Node) error {
 	case yaml.MappingNode:
 		var vv struct {
 			Name string
+			Sh   string
 			Enum []string
 		}
 		if err := node.Decode(&vv); err != nil {
@@ -60,6 +63,7 @@ func (v *VarsWithValidation) UnmarshalYAML(node *yaml.Node) error {
 		}
 		v.Name = vv.Name
 		v.Enum = vv.Enum
+		v.Sh = vv.Sh
 		return nil
 	}
 
diff --git a/testdata/interactive_vars/Taskfile.yml b/testdata/interactive_vars/Taskfile.yml
index 49f68a2fa1..f3c1388f9e 100644
--- a/testdata/interactive_vars/Taskfile.yml
+++ b/testdata/interactive_vars/Taskfile.yml
@@ -20,6 +20,15 @@ tasks:
     cmds:
       - echo "Deploying to {{.ENVIRONMENT}}..."
 
+  choose_file:
+    desc: Choose a file
+    requires:
+      vars:
+        - name: SELECTED_FILE
+          sh: printf "val1\nval2\nval3\n"
+    cmds:
+      - echo "You have selected {{.SELECTED_FILE}}"
+
   # Multiple variables at once
   release:
     desc: Create a release with version and environment
diff --git a/website/src/docs/guide.md b/website/src/docs/guide.md
index 6c3eb912bf..31257c9257 100644
--- a/website/src/docs/guide.md
+++ b/website/src/docs/guide.md
@@ -1243,9 +1243,11 @@ failing, you can enable interactive mode in your `.taskrc.yml`:
 interactive: true
 ```
 
-When enabled, Task will display an interactive prompt for any missing required
-variable. For variables with an `enum`, a selection menu is shown. For variables
-without an enum, a text input is displayed.
+When enabled, Task will display an interactive prompt for any missing required variable.
+Interactive variables can either be a simple text input or a select menu.
+
+The select menu presents a list of possible values to select from when a list of values is defined in an `enum` array, or dynamically with an `sh` script.
+When using an `sh` script the values need to be new line delimited.
 
 ```yaml
 # Taskfile.yml
@@ -1260,6 +1262,16 @@ tasks:
         - VERSION
     cmds:
       - echo "Deploying {{.VERSION}} to {{.ENVIRONMENT}}"
+  copy-file:
+    requires:
+      vars:
+        - name: SELECTED_FILE
+          sh: ls # will prompt to select from a list of files in your workdir
+        - name: ENVIRONMENT
+          sh: get_envs.sh # a script that returns a new line delimited list of available envs
+    cmds:
+      - echo "Deploying {{.SELECTED_FILE}} to {{.ENVIRONMENT}}"
+
 ```
 
 ```shell
diff --git a/website/src/docs/reference/schema.md b/website/src/docs/reference/schema.md
index d0d4286943..703312806d 100644
--- a/website/src/docs/reference/schema.md
+++ b/website/src/docs/reference/schema.md
@@ -655,7 +655,7 @@ tasks:
 #### `requires`
 
 - **Type**: `Requires`
-- **Description**: Required variables with optional enum validation
+- **Description**: Required variables with optional enum validation, or options read from `sh` script evaluation
 
 ```yaml
 tasks:
@@ -678,6 +678,19 @@ tasks:
     cmds:
       - echo "Deploying to {{.ENVIRONMENT}} with log level {{.LOG_LEVEL}}"
       - ./deploy.sh
+
+
+  # Requirements with options coming from a sh script
+  select-file:
+    requires:
+      vars:
+        - name: SELECTED_FILE
+          sh: ls
+        - name: DEPLOY_ENV
+          sh: get_envs.sh # Script should return \n separated vals
+    cmds:
+      - echo "You have selected file: {{.SELECTED_FILE}}"
+      - echo "You have selected env: {{.DEPLOY_ENV}}"
 ```
 
 See [Prompting for missing variables interactively](/docs/guide#prompting-for-missing-variables-interactively)
diff --git a/website/src/public/schema.json b/website/src/public/schema.json
index 28ae66110b..081d69f9fb 100644
--- a/website/src/public/schema.json
+++ b/website/src/public/schema.json
@@ -629,6 +629,18 @@
           "items": {
             "oneOf": [
               { "type": "string" },
+              {
+                "type": "object",
+                "properties": {
+                  "name": { "type": "string" },
+                  "sh": {
+                    "type": "string",
+                    "description": "The value will be treated as a command and the output assigned to the variable"
+                  }
+                },
+                "required": ["name"],
+                "additionalProperties": false
+              },
               {
                 "type": "object",
                 "properties": {