diff --git a/integration_tests/features/orb_pack.feature b/integration_tests/features/orb_pack.feature
index 0780e78dd..007c61fda 100644
--- a/integration_tests/features/orb_pack.feature
+++ b/integration_tests/features/orb_pack.feature
@@ -22,22 +22,27 @@ Feature: Orb pack
     And the exit status should be 0
 
   @mocked_home_directory
-  Scenario: Orb pack with multiple includes fails
+  Scenario: Orb pack with multiple includes
     Given a file named "src/@orb.yml" with:
     """
     commands:
         test:
           steps:
             - run:
-                command: <<include(script.sh)>> <<include(script.sh)>>
+                command: <<include(script.sh)>> <<include(script2.sh)>>
     """
-    Given a file named "src/script.sh" with "echo Hello, world!"
+    Given a file named "src/script.sh" with "echo Hello,"
+    Given a file named "src/script2.sh" with "world!"
     When I run `circleci orb pack src`
     Then the output should contain:
     """
-    Error: An unexpected error occurred: multiple include statements: '<<include(script.sh)>> <<include(script.sh)>>'
+    commands:
+        test:
+            steps:
+                - run:
+                    command: echo Hello, world!
     """
-    And the exit status should be 255
+    And the exit status should be 0
 
   @mocked_home_directory
   Scenario: Orb pack with include statement in bigger string
@@ -47,15 +52,19 @@ Feature: Orb pack
         test:
           steps:
             - run:
-                command: include <<include(script.sh)>>
+                command: echo "<<include(script.sh)>>"
     """
-    Given a file named "src/script.sh" with "echo Hello, world!"
+    Given a file named "src/script.sh" with "Hello, world!"
     When I run `circleci orb pack src`
     Then the output should contain:
     """
-    Error: An unexpected error occurred: entire string must be include statement: 'include <<include(script.sh)>>'
+    commands:
+        test:
+            steps:
+                - run:
+                    command: echo "Hello, world!"
     """
-    And the exit status should be 255
+    And the exit status should be 0
 
   @mocked_home_directory
   Scenario: Missing @orb.yml for orb packing
diff --git a/process/process.go b/process/process.go
index cb7745ae1..6b1753ca4 100644
--- a/process/process.go
+++ b/process/process.go
@@ -8,36 +8,27 @@ import (
 	"strings"
 )
 
-// MaybeIncludeFile replaces intsances of <<include(file)>> with the contents
+// MaybeIncludeFile replaces instances of <<include(file)>> with the contents
 // of "file", escaping instances of "<<" within the file before returning, when
 // the <<include()>> parameter is the string passed.
 func MaybeIncludeFile(s string, orbDirectory string) (string, error) {
 	// View: https://regexr.com/599mq
 	includeRegex := regexp.MustCompile(`<<[\s]*include\(([-\w\/\.]+)\)?[\s]*>>`)
 
-	// only find up to 2 matches, because we throw an error if we find >1
-	includeMatches := includeRegex.FindAllStringSubmatch(s, 2)
-	if len(includeMatches) > 1 {
-		return "", fmt.Errorf("multiple include statements: '%s'", s)
-	}
+	includeMatches := includeRegex.FindAllStringSubmatch(s, -1)
 
-	if len(includeMatches) == 1 {
-		match := includeMatches[0]
+	for _, match := range includeMatches {
 		fullMatch, subMatch := match[0], match[1]
 
-		// throw an error if the entire string wasn't matched
-		if fullMatch != s {
-			return "", fmt.Errorf("entire string must be include statement: '%s'", s)
-		}
-
 		filepath := filepath.Join(orbDirectory, subMatch)
 		file, err := ioutil.ReadFile(filepath)
+
 		if err != nil {
 			return "", fmt.Errorf("could not open %s for inclusion", filepath)
 		}
-		escaped := strings.ReplaceAll(string(file), "<<", "\\<<")
 
-		return escaped, nil
+		escaped := strings.ReplaceAll(string(file), "<<", "\\<<")
+		s = strings.ReplaceAll(s, fullMatch, escaped)
 	}
 
 	return s, nil
diff --git a/process/process_test.go b/process/process_test.go
new file mode 100644
index 000000000..23d8edc97
--- /dev/null
+++ b/process/process_test.go
@@ -0,0 +1,86 @@
+package process
+
+import (
+	"io/ioutil"
+	"os"
+	"testing"
+)
+
+func Test_MaybeIncludeFile(t *testing.T) {
+	testCases := []struct {
+		description string
+		template    string
+		expected    string
+		files       map[string]string
+		errExpected bool
+	}{
+		{
+			description: "File gets replaced",
+			template:    "<<include(example.txt)>>",
+			expected:    "world",
+			files: map[string]string{
+				"example.txt": "world",
+			},
+			errExpected: false,
+		},
+		{
+			description: "Partial line include",
+			template:    "hello <<include(example-2.txt)>>",
+			expected:    "hello world",
+			files: map[string]string{
+				"example-2.txt": "world",
+			},
+			errExpected: false,
+		},
+		{
+			description: "Multiple includes",
+			template:    "<<include(example-1.txt)>> <<include(example-2.txt)>>",
+			expected:    "hello world",
+			files: map[string]string{
+				"example-1.txt": "hello",
+				"example-2.txt": "world",
+			},
+			errExpected: false,
+		},
+		{
+			description: "File does not exist",
+			template:    "<<include(file-that-does-not-exist.txt)>>",
+			files:       map[string]string{},
+			errExpected: true,
+		},
+		{
+			description: "Included files are escaped",
+			template:    "<<include(example-1.txt)>> world",
+			expected:    "\\<< hello world",
+			files: map[string]string{
+				"example-1.txt": "<< hello",
+			},
+			errExpected: false,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.description, func(t *testing.T) {
+			dir, err := ioutil.TempDir("", "circleci-cli-test")
+			if err != nil {
+				t.Fatal(err)
+			}
+			defer os.RemoveAll(dir)
+			for name, content := range tc.files {
+				if err := ioutil.WriteFile(dir+"/"+name, []byte(content), 0644); err != nil {
+					t.Fatal(err)
+				}
+			}
+
+			orbDirectory := dir
+			res, err := MaybeIncludeFile(tc.template, orbDirectory)
+			if err != nil && !tc.errExpected {
+				t.Errorf("Unexpected error: %v", err)
+			}
+
+			if !tc.errExpected && res != tc.expected {
+				t.Errorf("expected '%s', got '%s'", tc.expected, res)
+			}
+		})
+	}
+}