diff --git a/src/login/login.ts b/src/login/login.ts
index b93e07f1..1ba342b1 100644
--- a/src/login/login.ts
+++ b/src/login/login.ts
@@ -65,6 +65,125 @@ const {
   deleteTypeIndexRegistration
 } = solidLogicSingleton.typeIndex
 
+function formatDynamicError (error: unknown, contextLabel: string): string {
+  const e = error as any
+  const name = e?.name || 'Error'
+  const status = typeof e?.status === 'number' ? ` (HTTP ${e.status})` : ''
+  const message = e?.message
+    ? String(e.message)
+    : (typeof error === 'string' ? error : 'No additional details provided')
+  return `${contextLabel}: ${name}${status} - ${message}`
+}
+
+function guessPreferencesFileUri (me: NamedNode): string {
+  return me.uri
+    .replace('/profile/', '/')
+    .replace('/public/', '/')
+    .split('/')
+    .slice(0, -1)
+    .join('/') + '/settings/prefs.ttl'
+}
+
+function getMissingPreferencesFileUri (context: AuthenticationContext, err: unknown): string | null {
+  const responseUrl = (err as any)?.response?.url
+  if (typeof responseUrl === 'string' && responseUrl) {
+    return responseUrl
+  }
+  if (context.me) {
+    const pointer = store.any(
+      context.me,
+      ns.space('preferencesFile'),
+      undefined,
+      context.me.doc ? context.me.doc() : undefined
+    ) as NamedNode | null
+    if (pointer?.uri) {
+      return pointer.uri
+    }
+    return guessPreferencesFileUri(context.me as NamedNode)
+  }
+  return null
+}
+
+async function ensurePreferencesFileRowInProfile (
+  me: NamedNode,
+  prefsNode: NamedNode,
+  profileDoc: NamedNode
+): Promise<void> {
+  const existingPreferencesFile = store.any(me, ns.space('preferencesFile'), undefined, profileDoc)
+
+  if (existingPreferencesFile && existingPreferencesFile.equals(prefsNode)) {
+    return
+  }
+
+  if (!store.updater) {
+    throw new Error('Cannot create preferences file: store has no updater')
+  }
+
+  const deletions = existingPreferencesFile
+    ? [st(me, ns.space('preferencesFile'), existingPreferencesFile, profileDoc)]
+    : []
+  const insertions = [st(me, ns.space('preferencesFile'), prefsNode, profileDoc)]
+
+  await new Promise<void>((resolve, reject) => {
+    store.updater!.update(deletions as any, insertions as any, (_uri, ok, body) => {
+      if (ok) {
+        resolve()
+      } else {
+        reject(new Error(body || 'Unable to update preferencesFile in WebID profile'))
+      }
+    })
+  })
+}
+
+function buildPreferencesFileTurtle (me: NamedNode): string {
+  const mbox = store.any(me, ns.foaf('mbox'))
+  const mboxLine = mbox ? `\n<${me.uri}> foaf:mbox <${mbox.value}> .\n` : '\n'
+
+  return (
+    '@prefix dct: <http://purl.org/dc/terms/>.\n' +
+    '@prefix pim: <http://www.w3.org/ns/pim/space#>.\n' +
+    '@prefix foaf: <http://xmlns.com/foaf/0.1/>.\n' +
+    '@prefix solid: <http://www.w3.org/ns/solid/terms#>.\n\n' +
+    '<>\n' +
+    '  a pim:ConfigurationFile;\n\n' +
+    '  dct:title "Preferences file" .\n' +
+    mboxLine +
+    `<${me.uri}>\n` +
+    '  solid:publicTypeIndex <publicTypeIndex.ttl> ;\n' +
+    '  solid:privateTypeIndex <privateTypeIndex.ttl> .\n'
+  )
+}
+
+async function writePreferencesFileDocument (uri: string, data: string): Promise<void> {
+  if (!store.fetcher) {
+    throw new Error('Cannot create preferences file: store has no fetcher')
+  }
+
+  await store.fetcher.webOperation('PUT', uri, {
+    data,
+    contentType: 'text/turtle'
+  })
+}
+
+async function createPreferencesFile (context: AuthenticationContext, uri: string): Promise<void> {
+  const me = (context.me as NamedNode) || authn.currentUser()
+  if (!me) {
+    throw new Error('Cannot create preferences file: no logged-in WebID')
+  }
+  context.me = me
+
+  const profileDoc = me.doc()
+  const prefsNode = store.sym(uri)
+
+  await ensurePreferencesFileRowInProfile(me, prefsNode, profileDoc)
+
+  const prefsTurtle = buildPreferencesFileTurtle(me)
+  await writePreferencesFileDocument(uri, prefsTurtle)
+
+  context.preferencesFile = await loadPreferences(me)
+  context.preferencesFileError = undefined
+}
+
 /**
  * Resolves with the logged in user's WebID
  *
@@ -125,6 +244,11 @@ export async function ensureLoadedPreferences (
   } */
   try {
     context = await ensureLoadedProfile(context)
+    if (!context.me) {
+      context.preferencesFileError = 'Not logged in, so preferences were not loaded.'
+      debug.log('not logged in, no preferences loaded')
+      return context
+    }
 
     // console.log('back in Solid UI after logInLoadProfile', context)
     const preferencesFile = await loadPreferences(context.me as NamedNode)
@@ -137,30 +261,63 @@ export async function ensureLoadedPreferences (
     if (err instanceof UnauthorizedError) {
       m2 =
         'Oops — you are not authenticated (properly logged in), so SolidOS cannot read your preferences file. Try logging out and then logging back in.'
+      context.preferencesFileError = m2
       alert(m2)
+      return context
     } else if (err instanceof CrossOriginForbiddenError) {
-      m2 = `Unauthorized: Assuming preference file blocked for origin ${window.location.origin}`
+      m2 = `Blocked by origin: preference file request from ${window.location.origin} was forbidden. Ensure this app origin is trusted/allowed for your preferences file.`
       context.preferencesFileError = m2
       return context
     } else if (err instanceof SameOriginForbiddenError) {
       m2 =
-        'You are not authorized to read your preference file. This may be because you are using an untrusted web app.'
+        'You are not authorized to read your preference file from this app context.'
+      context.preferencesFileError = m2
       debug.warn(m2)
       return context
     } else if (err instanceof NotEditableError) {
       m2 =
-        'You are not authorized to edit your preference file. This may be because you are using an untrusted web app.'
+        'You are not authorized to edit your preference file from this app context.'
+      context.preferencesFileError = m2
       debug.warn(m2)
       return context
     } else if (err instanceof WebOperationError) {
-      m2 =
-        'You are not authorized to edit your preference file. This may be because you are using an untrusted web app.'
+      m2 = formatDynamicError(err, 'Preference file web operation failed')
+      context.preferencesFileError = m2
       debug.warn(m2)
+      return context
     } else if (err instanceof FetchError) {
-      m2 = `Strange: Error ${err.status} trying to read your preference file.${err.message}`
+      if (err.status === 404) {
+        m2 = 'Your preferences file was not found (404). It may not exist yet.'
+        debug.warn(m2)
+        const missingPreferencesFileUri = getMissingPreferencesFileUri(context, err)
+        if (missingPreferencesFileUri) {
+          try {
+            await createPreferencesFile(context, missingPreferencesFileUri)
+            debug.log(`Preferences file created automatically: ${missingPreferencesFileUri}`)
+            return context
+          } catch (createError) {
+            const message = formatDynamicError(createError, 'Failed to create preferences file automatically')
+            context.preferencesFileError = message
+            debug.error(message)
+            if (context.div && context.dom) {
+              context.div.appendChild(widgets.errorMessageBlock(context.dom, message))
+            }
+            return context
+          }
+        }
+        context.preferencesFileError = m2
+        return context
+      }
+      m2 = formatDynamicError(err, 'Error reading your preferences file')
+      context.preferencesFileError = m2
+      debug.warn(m2)
       alert(m2)
+      return context
     } else {
-      throw new Error(`(via loadPrefs) ${err}`)
+      m2 = formatDynamicError(err, 'Unexpected error while loading preferences')
+      context.preferencesFileError = m2
+      debug.error(m2)
+      return context
     }
   }
   return context
@@ -183,14 +340,17 @@ export async function ensureLoadedProfile (
   try {
     const logInContext = await ensureLoggedIn(context)
     if (!logInContext.me) {
-      throw new Error('Could not log in')
+      const message = 'Could not log in; skipping profile load.'
+      debug.log(message)
+      throw new Error(message)
     }
     context.publicProfile = await loadProfile(logInContext.me)
   } catch (err) {
+    const message = formatDynamicError(err, 'Unable to load your profile')
     if (context.div && context.dom) {
-      context.div.appendChild(widgets.errorMessageBlock(context.dom, err.message))
+      context.div.appendChild(widgets.errorMessageBlock(context.dom, message))
     }
-    throw new Error(`Can't log in: ${err}`)
+    throw new Error(message)
   }
   return context
 }
@@ -1049,9 +1209,13 @@ export function newAppInstance (
 export async function getUserRoles (): Promise<Array<NamedNode>> {
   try {
     const { me, preferencesFile, preferencesFileError } = await ensureLoadedPreferences({})
-    if (!preferencesFile || preferencesFileError) {
+    if (preferencesFileError) {
       throw new Error(preferencesFileError)
     }
+    if (!preferencesFile) {
+      const authState = me ? `logged in as ${me.value || me.uri}` : 'not logged in'
+      throw new Error(`Preferences file unavailable (${authState})`)
+    }
     return solidLogicSingleton.store.each(
       me,
       ns.rdf('type'),
@@ -1059,7 +1223,7 @@ export async function getUserRoles (): Promise<Array<NamedNode>> {
       preferencesFile.doc()
     ) as NamedNode[]
   } catch (error) {
-    debug.warn('Unable to fetch your preferences - this was the error: ', error)
+    debug.warn(formatDynamicError(error, 'Unable to fetch your preferences'))
   }
   return []
 }