diff --git a/package.json b/package.json
index 71becb367..5f5fccb45 100644
--- a/package.json
+++ b/package.json
@@ -1,7 +1,7 @@
 {
   "name": "@oclif/core",
   "description": "base library for oclif CLIs",
-  "version": "2.8.0",
+  "version": "2.8.1-beta.0",
   "author": "Salesforce",
   "bugs": "https://github.com/oclif/core/issues",
   "dependencies": {
@@ -114,4 +114,4 @@
     "pretest": "yarn build --noEmit && tsc -p test --noEmit --skipLibCheck"
   },
   "types": "lib/index.d.ts"
-}
\ No newline at end of file
+}
diff --git a/src/parser/parse.ts b/src/parser/parse.ts
index 8349a91c8..f6fd34493 100644
--- a/src/parser/parse.ts
+++ b/src/parser/parse.ts
@@ -218,17 +218,6 @@ export class Parser<T extends ParserInput, TFlags extends OutputFlags<T['flags']
 
       if (!flag) throw new CLIError(`Unexpected flag ${token.flag}`)
 
-      // if flag has defaultHelp, capture its value into metadata
-      if (Reflect.has(flag, 'defaultHelp')) {
-        try {
-          const defaultHelpProperty = Reflect.get(flag, 'defaultHelp')
-          const defaultHelp = (typeof defaultHelpProperty === 'function' ? await defaultHelpProperty({options: flag, flags, ...this.context}) : defaultHelpProperty)
-          this.metaData.flags[token.flag] = {...this.metaData.flags[token.flag], defaultHelp}
-        } catch {
-          // no-op
-        }
-      }
-
       if (flag.type === 'boolean') {
         if (token.input === `--no-${flag.name}`) {
           flags[token.flag] = false
@@ -284,9 +273,25 @@ export class Parser<T extends ParserInput, TFlags extends OutputFlags<T['flags']
 
       if (!(k in flags) && flag.default !== undefined) {
         this.metaData.flags[k] = {...this.metaData.flags[k], setFromDefault: true}
-        const defaultValue = (typeof flag.default === 'function' ? await flag.default({options: flag, flags, ...this.context}) : flag.default)
+        const defaultValue = (typeof flag.default === 'function' ? await flag.default({
+          options: flag,
+          flags, ...this.context,
+        }) : flag.default)
         flags[k] = defaultValue
       }
+
+      if ((k in flags) && Reflect.has(flag, 'defaultHelp')) {
+        try {
+          const defaultHelpProperty = Reflect.get(flag, 'defaultHelp')
+          const defaultHelp = (typeof defaultHelpProperty === 'function' ? await defaultHelpProperty({
+            options: flag,
+            flags, ...this.context,
+          }) : defaultHelpProperty)
+          this.metaData.flags[k] = {...this.metaData.flags[k], defaultHelp}
+        } catch {
+          // no-op
+        }
+      }
     }
 
     return flags
diff --git a/test/parser/parse.test.ts b/test/parser/parse.test.ts
index aa9246de7..503254a48 100644
--- a/test/parser/parse.test.ts
+++ b/test/parser/parse.test.ts
@@ -727,7 +727,7 @@ See more help with --help`)
           expect.fail(`Should have thrown an error ${JSON.stringify(out)}`)
         } catch (error) {
           assert(error instanceof Error)
-          expect(error.message).to.include('--foo=bar cannot also be provided when using --bar')
+          expect(error.message).to.include('--foo=baz cannot also be provided when using --bar')
         }
       })
       it('should error with exclusive flag violation and defaultHelp value', async () => {