diff --git a/src/errors/pretty-print.ts b/src/errors/pretty-print.ts
index a5f8ee3..e1de26d 100644
--- a/src/errors/pretty-print.ts
+++ b/src/errors/pretty-print.ts
@@ -23,40 +23,49 @@ export interface PrettyPrintableError {
   /**
    * a suggestion that may be useful or provide additional context
    */
-  suggestion?: string;
+  suggestions?: string[];
 }
 
 // These exist for backwards compatibility with CLIError
 type CLIErrorDisplayOptions = { name?: string; bang?: string }
 
 export function applyPrettyPrintOptions(error: Error, options: PrettyPrintableError): PrettyPrintableError {
-  const prettyErrorKeys: (keyof PrettyPrintableError)[] = ['message', 'code', 'ref', 'suggestion']
+  const prettyErrorKeys: (keyof PrettyPrintableError)[] = ['message', 'code', 'ref', 'suggestions']
 
   prettyErrorKeys.forEach(key => {
     const applyOptionsKey = !(key in error) && options[key]
     if (applyOptionsKey) {
-      (error as PrettyPrintableError)[key] = options[key]
+      (error as any)[key] = options[key]
     }
   })
 
   return error
 }
 
+const formatSuggestions = (suggestions?: string[]): string | undefined => {
+  const label = 'Try this:'
+  if (!suggestions || suggestions.length === 0) return undefined
+  if (suggestions.length === 1) return `${label} ${suggestions[0]}`
+
+  const multiple = suggestions.map(suggestion => `* ${suggestion}`).join('\n')
+  return `${label}\n${indent(multiple, 2)}`
+}
+
 export default function prettyPrint(error: Error & PrettyPrintableError & CLIErrorDisplayOptions) {
   if (config.debug) {
     return error.stack
   }
 
-  const {message, code, suggestion, ref, name: errorSuffix, bang} = error
+  const {message, code, suggestions, ref, name: errorSuffix, bang} = error
 
   // errorSuffix is pulled from the 'name' property on CLIError
   // and is like either Error or Warning
   const formattedHeader = message ? `${errorSuffix || 'Error'}: ${message}` : undefined
   const formattedCode = code ? `Code: ${code}` : undefined
-  const formattedSuggestion = suggestion ? `Suggestion: ${suggestion}` : undefined
+  const formattedSuggestions = formatSuggestions(suggestions)
   const formattedReference = ref ? `Reference: ${ref}` : undefined
 
-  const formatted = [formattedHeader, formattedCode, formattedSuggestion, formattedReference]
+  const formatted = [formattedHeader, formattedCode, formattedSuggestions, formattedReference]
   .filter(Boolean)
   .join('\n')
 
diff --git a/test/error.test.ts b/test/error.test.ts
index 5134c16..0bdca26 100644
--- a/test/error.test.ts
+++ b/test/error.test.ts
@@ -14,25 +14,25 @@ describe('error', () => {
 
   fancy
   .do(() => {
-    error('An error happened!', {code: 'ERR', ref: 'https://oclif.com/error', suggestion: 'rm -rf node_modules'})
+    error('An error happened!', {code: 'ERR', ref: 'https://oclif.com/error', suggestions: ['rm -rf node_modules']})
   })
   .catch((error: PrettyPrintableError) => {
     expect(error.message).to.equal('An error happened!')
     expect(error.code).to.equal('ERR')
     expect(error.ref).to.equal('https://oclif.com/error')
-    expect(error.suggestion).to.equal('rm -rf node_modules')
+    expect(error.suggestions).to.deep.equal(['rm -rf node_modules'])
   })
   .it('attaches pretty print properties to a new error from options')
 
   fancy
   .do(() => {
-    error(new Error('An existing error object error!'), {code: 'ERR', ref: 'https://oclif.com/error', suggestion: 'rm -rf node_modules'})
+    error(new Error('An existing error object error!'), {code: 'ERR', ref: 'https://oclif.com/error', suggestions: ['rm -rf node_modules']})
   })
   .catch((error: PrettyPrintableError) => {
     expect(error.message).to.equal('An existing error object error!')
     expect(error.code).to.equal('ERR')
     expect(error.ref).to.equal('https://oclif.com/error')
-    expect(error.suggestion).to.equal('rm -rf node_modules')
+    expect(error.suggestions).to.deep.equal(['rm -rf node_modules'])
   })
   .it('attached pretty print properties from options to an existing error object')
 
@@ -41,13 +41,13 @@ describe('error', () => {
     const e: any = new Error('An existing error object error!')
     e.code = 'ORIG_ERR'
     e.ref = 'ORIG_REF'
-    e.suggestion = 'ORIG_SUGGESTION'
-    error(e, {code: 'ERR', ref: 'https://oclif.com/error', suggestion: 'rm -rf node_modules'})
+    e.suggestions = ['ORIG_SUGGESTION']
+    error(e, {code: 'ERR', ref: 'https://oclif.com/error', suggestions: ['rm -rf node_modules']})
   })
   .catch((error: PrettyPrintableError) => {
     expect(error.code).to.equal('ORIG_ERR')
     expect(error.ref).to.equal('ORIG_REF')
-    expect(error.suggestion).to.equal('ORIG_SUGGESTION')
+    expect(error.suggestions).to.deep.equal(['ORIG_SUGGESTION'])
   })
   .it('preserves original pretty printable properties and is not overwritten by options')
 
diff --git a/test/pretty-print.test.ts b/test/pretty-print.test.ts
index 19c2e7f..c35af95 100644
--- a/test/pretty-print.test.ts
+++ b/test/pretty-print.test.ts
@@ -10,16 +10,28 @@ describe('pretty-print', () => {
     const sampleError: Error & PrettyPrintableError = new Error('Something very serious has gone wrong with the flags!')
     sampleError.ref = 'https://oclif.io/docs/flags'
     sampleError.code = 'OCLIF_BAD_FLAG'
-    sampleError.suggestion = 'Try using using a good flag'
+    sampleError.suggestions = ['Try using using a good flag']
 
     expect(
       stripAnsi(prettyPrint(sampleError)),
     ).to.equal(`    Error: Something very serious has gone wrong with the flags!
     Code: OCLIF_BAD_FLAG
-    Suggestion: Try using using a good flag
+    Try this: Try using using a good flag
     Reference: https://oclif.io/docs/flags`)
   })
 
+  fancy
+  .it('pretty prints multiple suggestions', async () => {
+    const sampleError: Error & PrettyPrintableError = new Error('Something very serious has gone wrong with the flags!')
+    sampleError.suggestions = ['Use a good flag', 'Use no flags']
+    expect(
+      stripAnsi(prettyPrint(sampleError)),
+    ).to.equal(`    Error: Something very serious has gone wrong with the flags!
+    Try this:
+      * Use a good flag
+      * Use no flags`)
+  })
+
   fancy
   .it('pretty prints with omitted fields', async () => {
     const sampleError = new Error('Something very serious has gone wrong with the flags!')