diff --git a/lib/commands/help-search.js b/lib/commands/help-search.js
index 23b426eaa016d..488189bbbc5cd 100644
--- a/lib/commands/help-search.js
+++ b/lib/commands/help-search.js
@@ -6,6 +6,8 @@ const glob = promisify(require('glob'))
 const readFile = promisify(fs.readFile)
 const BaseCommand = require('../base-command.js')
 
+const globify = pattern => pattern.split('\\').join('/')
+
 class HelpSearch extends BaseCommand {
   static description = 'Search npm help documentation'
   static name = 'help-search'
@@ -19,7 +21,7 @@ class HelpSearch extends BaseCommand {
     }
 
     const docPath = path.resolve(__dirname, '..', '..', 'docs/content')
-    const files = await glob(`${docPath}/*/*.md`)
+    const files = await glob(`${globify(docPath)}/*/*.md`)
     const data = await this.readFiles(files)
     const results = await this.searchFiles(args, data, files)
     const formatted = this.formatResults(args, results)
diff --git a/lib/commands/help.js b/lib/commands/help.js
index d31b3ca697651..e7d6395a1b01a 100644
--- a/lib/commands/help.js
+++ b/lib/commands/help.js
@@ -5,6 +5,7 @@ const { promisify } = require('util')
 const glob = promisify(require('glob'))
 const localeCompare = require('@isaacs/string-locale-compare')('en')
 
+const globify = pattern => pattern.split('\\').join('/')
 const BaseCommand = require('../base-command.js')
 
 // Strips out the number from foo.7 or foo.7. or foo.7.tgz
@@ -26,7 +27,7 @@ class Help extends BaseCommand {
       return []
     }
     const g = path.resolve(__dirname, '../../man/man[0-9]/*.[0-9]')
-    const files = await glob(g)
+    const files = await glob(globify(g))
 
     return Object.keys(files.reduce(function (acc, file) {
       file = path.basename(file).replace(/\.[0-9]+$/, '')
@@ -61,7 +62,7 @@ class Help extends BaseCommand {
     const manroot = path.resolve(__dirname, '..', '..', 'man')
     // find either section.n or npm-section.n
     const f = `${manroot}/${manSearch}/?(npm-)${section}.[0-9]*`
-    let mans = await glob(f)
+    let mans = await glob(globify(f))
     mans = mans.sort((a, b) => {
       // Prefer the page with an npm prefix, if there's only one.
       const aHasPrefix = manNpmPrefixRegex.test(a)
diff --git a/lib/utils/log-file.js b/lib/utils/log-file.js
index 282c72700e58e..9cf6513bedf48 100644
--- a/lib/utils/log-file.js
+++ b/lib/utils/log-file.js
@@ -9,6 +9,7 @@ const fs = require('@npmcli/fs')
 const log = require('./log-shim')
 
 const padZero = (n, length) => n.toString().padStart(length.toString().length, '0')
+const globify = pattern => pattern.split('\\').join('/')
 
 const _logHandler = Symbol('logHandler')
 const _formatLogItem = Symbol('formatLogItem')
@@ -225,7 +226,7 @@ class LogFiles {
       )
 
       // Always ignore the currently written files
-      const files = await glob(logGlob, { ignore: this.#files })
+      const files = await glob(globify(logGlob), { ignore: this.#files.map(globify) })
       const toDelete = files.length - this.#logsMax
 
       if (toDelete <= 0) {
@@ -236,7 +237,7 @@ class LogFiles {
 
       for (const file of files.slice(0, toDelete)) {
         try {
-          await rimraf(file)
+          await rimraf(file, { glob: false })
         } catch (e) {
           log.silly('logfile', 'error removing log file', file, e)
         }