diff --git a/services/clsi/app/js/ContentCacheManager.js b/services/clsi/app/js/ContentCacheManager.js
index 2096e1afc7..d424681615 100644
--- a/services/clsi/app/js/ContentCacheManager.js
+++ b/services/clsi/app/js/ContentCacheManager.js
@@ -7,6 +7,7 @@ const fs = require('fs')
 const crypto = require('crypto')
 const Path = require('path')
 const Settings = require('settings-sharelatex')
+const pLimit = require('p-limit')
 
 const MIN_CHUNK_SIZE = Settings.pdfCachingMinChunkSize
 
@@ -25,7 +26,10 @@ async function update(contentDir, filePath) {
   const extractor = new PdfStreamsExtractor()
   const ranges = []
   const newRanges = []
-  const seenHashes = new Set()
+  // keep track of hashes expire old ones when they reach a generation > N.
+  const tracker = await HashFileTracker.from(contentDir)
+  tracker.updateAge()
+
   for await (const chunk of stream) {
     const pdfStreams = extractor.consume(chunk)
     for (const pdfStream of pdfStreams) {
@@ -36,15 +40,106 @@ async function update(contentDir, filePath) {
       ranges.push(range)
 
       // Optimization: Skip writing of duplicate streams.
-      if (seenHashes.has(hash)) continue
-      seenHashes.add(hash)
+      if (tracker.track(range)) continue
 
-      if (await writePdfStream(contentDir, hash, pdfStream.buffers)) {
-        newRanges.push(range)
-      }
+      await writePdfStream(contentDir, hash, pdfStream.buffers)
+      newRanges.push(range)
     }
   }
-  return [ranges, newRanges]
+  const reclaimedSpace = await tracker.deleteStaleHashes(5)
+  await tracker.flush()
+  return [ranges, newRanges, reclaimedSpace]
+}
+
+function getStatePath(contentDir) {
+  return Path.join(contentDir, '.state.v0.json')
+}
+
+class HashFileTracker {
+  constructor(contentDir, { hashAge = [], hashSize = [] }) {
+    this.contentDir = contentDir
+    this.hashAge = new Map(hashAge)
+    this.hashSize = new Map(hashSize)
+  }
+
+  static async from(contentDir) {
+    const statePath = getStatePath(contentDir)
+    let state = {}
+    try {
+      const blob = await fs.promises.readFile(statePath)
+      state = JSON.parse(blob)
+    } catch (e) {}
+    return new HashFileTracker(contentDir, state)
+  }
+
+  track(range) {
+    const exists = this.hashAge.has(range.hash)
+    if (!exists) {
+      this.hashSize.set(range.hash, range.end - range.start)
+    }
+    this.hashAge.set(range.hash, 0)
+    return exists
+  }
+
+  updateAge() {
+    for (const [hash, age] of this.hashAge) {
+      this.hashAge.set(hash, age + 1)
+    }
+    return this
+  }
+
+  findStale(maxAge) {
+    const stale = []
+    for (const [hash, age] of this.hashAge) {
+      if (age > maxAge) {
+        stale.push(hash)
+      }
+    }
+    return stale
+  }
+
+  async flush() {
+    const statePath = getStatePath(this.contentDir)
+    const blob = JSON.stringify({
+      hashAge: Array.from(this.hashAge.entries()),
+      hashSize: Array.from(this.hashSize.entries())
+    })
+    const atomicWrite = statePath + '~'
+    try {
+      await fs.promises.writeFile(atomicWrite, blob)
+    } catch (err) {
+      try {
+        await fs.promises.unlink(atomicWrite)
+      } catch (e) {}
+      throw err
+    }
+    try {
+      await fs.promises.rename(atomicWrite, statePath)
+    } catch (err) {
+      try {
+        await fs.promises.unlink(atomicWrite)
+      } catch (e) {}
+      throw err
+    }
+  }
+
+  async deleteStaleHashes(n) {
+    // delete any hash file older than N generations
+    const hashes = this.findStale(n)
+
+    let reclaimedSpace = 0
+    if (hashes.length === 0) {
+      return reclaimedSpace
+    }
+
+    await promiseMapWithLimit(10, hashes, async (hash) => {
+      await fs.promises.unlink(Path.join(this.contentDir, hash))
+      this.hashAge.delete(hash)
+      reclaimedSpace += this.hashSize.get(hash)
+      this.hashSize.delete(hash)
+    })
+    return reclaimedSpace
+  }
 }
 
 class PdfStreamsExtractor {
@@ -121,13 +216,6 @@ function pdfStreamHash(buffers) {
 
 async function writePdfStream(dir, hash, buffers) {
   const filename = Path.join(dir, hash)
-  try {
-    await fs.promises.stat(filename)
-    // The file exists. Do not rewrite the content.
-    // It would change the modified-time of the file and hence invalidate the
-    //  ETags used for client side caching via browser internals.
-    return false
-  } catch (e) {}
   const atomicWriteFilename = filename + '~'
   const file = await fs.promises.open(atomicWriteFilename, 'w')
   if (Settings.enablePdfCachingDark) {
@@ -150,7 +238,11 @@ async function writePdfStream(dir, hash, buffers) {
       throw err
     }
   }
-  return true
+}
+
+function promiseMapWithLimit(concurrency, array, fn) {
+  const limit = pLimit(concurrency)
+  return Promise.all(array.map((x) => limit(() => fn(x))))
 }
 
 module.exports = {
diff --git a/services/clsi/app/js/ContentCacheMetrics.js b/services/clsi/app/js/ContentCacheMetrics.js
index 04b475f827..f5f9188ddc 100644
--- a/services/clsi/app/js/ContentCacheMetrics.js
+++ b/services/clsi/app/js/ContentCacheMetrics.js
@@ -72,7 +72,10 @@ function emitPdfCachingStats(stats, timings) {
 
   // How much space do the ranges use?
   // This will accumulate the ranges size over time, skipping already written ranges.
-  Metrics.summary('pdf-ranges-disk-size', stats['pdf-caching-new-ranges-size'])
+  Metrics.summary(
+    'pdf-ranges-disk-size',
+    stats['pdf-caching-new-ranges-size'] - stats['pdf-caching-reclaimed-space']
+  )
 }
 
 module.exports = {
diff --git a/services/clsi/app/js/OutputCacheManager.js b/services/clsi/app/js/OutputCacheManager.js
index fe23ae3e3c..e6167570f8 100644
--- a/services/clsi/app/js/OutputCacheManager.js
+++ b/services/clsi/app/js/OutputCacheManager.js
@@ -278,10 +278,10 @@ module.exports = OutputCacheManager = {
         const timer = new Metrics.Timer('compute-pdf-ranges')
         ContentCacheManager.update(contentDir, outputFilePath, function (
           err,
-          ranges
+          result
         ) {
           if (err) return callback(err, outputFiles)
-          const [contentRanges, newContentRanges] = ranges
+          const [contentRanges, newContentRanges, reclaimedSpace] = result
 
           if (Settings.enablePdfCachingDark) {
             // In dark mode we are doing the computation only and do not emit
@@ -302,6 +302,7 @@ module.exports = OutputCacheManager = {
             (sum, next) => sum + (next.end - next.start),
             0
           )
+          stats['pdf-caching-reclaimed-space'] = reclaimedSpace
           callback(null, outputFiles)
         })
       } else {
diff --git a/services/clsi/package-lock.json b/services/clsi/package-lock.json
index 4a662040da..773d9f4319 100644
--- a/services/clsi/package-lock.json
+++ b/services/clsi/package-lock.json
@@ -1066,6 +1066,12 @@
       "resolved": "https://registry.npmjs.org/@protobufjs/utf8/-/utf8-1.1.0.tgz",
       "integrity": "sha1-p3c2C1s5oaLlEG+OhY8v0tBgxXA="
     },
+    "@sindresorhus/is": {
+      "version": "0.14.0",
+      "resolved": "https://registry.npmjs.org/@sindresorhus/is/-/is-0.14.0.tgz",
+      "integrity": "sha512-9NET910DNaIPngYnLLPeg+Ogzqsi9uM4mSboU5y6p8S5DzMTVEsJZrawi+BoDNUVBa2DhJqQYUFvMDfgU062LQ==",
+      "dev": true
+    },
     "@sinonjs/commons": {
       "version": "1.7.1",
       "resolved": "https://registry.npmjs.org/@sinonjs/commons/-/commons-1.7.1.tgz",
@@ -1127,6 +1133,15 @@
       "integrity": "sha512-+iTbntw2IZPb/anVDbypzfQa+ay64MW0Zo8aJ8gZPWMMK6/OubMVb6lUPMagqjOPnmtauXnFCACVl3O7ogjeqQ==",
       "dev": true
     },
+    "@szmarczak/http-timer": {
+      "version": "1.1.2",
+      "resolved": "https://registry.npmjs.org/@szmarczak/http-timer/-/http-timer-1.1.2.tgz",
+      "integrity": "sha512-XIB2XbzHTN6ieIjfIMV9hlVcfPU26s2vafYWQcZHWXHOxiaRZYEDKEwdl129Zyg50+foYV2jCgtrqSA6qNuNSA==",
+      "dev": true,
+      "requires": {
+        "defer-to-connect": "^1.0.1"
+      }
+    },
     "@tootallnate/once": {
       "version": "1.1.2",
       "resolved": "https://registry.npmjs.org/@tootallnate/once/-/once-1.1.2.tgz",
@@ -1276,6 +1291,55 @@
         "uri-js": "^4.2.2"
       }
     },
+    "ansi-align": {
+      "version": "3.0.0",
+      "resolved": "https://registry.npmjs.org/ansi-align/-/ansi-align-3.0.0.tgz",
+      "integrity": "sha512-ZpClVKqXN3RGBmKibdfWzqCY4lnjEuoNzU5T0oEFpfd/z5qJHVarukridD4juLO2FXMiwUQxr9WqQtaYa8XRYw==",
+      "dev": true,
+      "requires": {
+        "string-width": "^3.0.0"
+      },
+      "dependencies": {
+        "ansi-regex": {
+          "version": "4.1.0",
+          "resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-4.1.0.tgz",
+          "integrity": "sha512-1apePfXM1UOSqw0o9IiFAovVz9M5S1Dg+4TrDwfMewQ6p/rmMueb7tWZjQ1rx4Loy1ArBggoqGpfqqdI4rondg==",
+          "dev": true
+        },
+        "emoji-regex": {
+          "version": "7.0.3",
+          "resolved": "https://registry.npmjs.org/emoji-regex/-/emoji-regex-7.0.3.tgz",
+          "integrity": "sha512-CwBLREIQ7LvYFB0WyRvwhq5N5qPhc6PMjD6bYggFlI5YyDgl+0vxq5VHbMOFqLg7hfWzmu8T5Z1QofhmTIhItA==",
+          "dev": true
+        },
+        "is-fullwidth-code-point": {
+          "version": "2.0.0",
+          "resolved": "https://registry.npmjs.org/is-fullwidth-code-point/-/is-fullwidth-code-point-2.0.0.tgz",
+          "integrity": "sha1-o7MKXE8ZkYMWeqq5O+764937ZU8=",
+          "dev": true
+        },
+        "string-width": {
+          "version": "3.1.0",
+          "resolved": "https://registry.npmjs.org/string-width/-/string-width-3.1.0.tgz",
+          "integrity": "sha512-vafcv6KjVZKSgz06oM/H6GDBrAtz8vdhQakGjFIvNrHA6y3HCF1CInLy+QLq8dTJPQ1b+KDUqDFctkdRW44e1w==",
+          "dev": true,
+          "requires": {
+            "emoji-regex": "^7.0.1",
+            "is-fullwidth-code-point": "^2.0.0",
+            "strip-ansi": "^5.1.0"
+          }
+        },
+        "strip-ansi": {
+          "version": "5.2.0",
+          "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-5.2.0.tgz",
+          "integrity": "sha512-DuRs1gKbBqsMKIZlrffwlug8MHkcnpjs5VPmL1PAh+mA30U0DTotfDZ0d2UUsXpPmPmMMJ6W773MaA3J+lbiWA==",
+          "dev": true,
+          "requires": {
+            "ansi-regex": "^4.1.0"
+          }
+        }
+      }
+    },
     "ansi-colors": {
       "version": "3.2.3",
       "resolved": "https://registry.npmjs.org/ansi-colors/-/ansi-colors-3.2.3.tgz",
@@ -1587,6 +1651,105 @@
       "integrity": "sha1-tcCeF8rNET0Rt7s+04TMASmU2Gs=",
       "dev": true
     },
+    "boxen": {
+      "version": "4.2.0",
+      "resolved": "https://registry.npmjs.org/boxen/-/boxen-4.2.0.tgz",
+      "integrity": "sha512-eB4uT9RGzg2odpER62bBwSLvUeGC+WbRjjyyFhGsKnc8wp/m0+hQsMUvUe3H2V0D5vw0nBdO1hCJoZo5mKeuIQ==",
+      "dev": true,
+      "requires": {
+        "ansi-align": "^3.0.0",
+        "camelcase": "^5.3.1",
+        "chalk": "^3.0.0",
+        "cli-boxes": "^2.2.0",
+        "string-width": "^4.1.0",
+        "term-size": "^2.1.0",
+        "type-fest": "^0.8.1",
+        "widest-line": "^3.1.0"
+      },
+      "dependencies": {
+        "ansi-regex": {
+          "version": "5.0.0",
+          "resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-5.0.0.tgz",
+          "integrity": "sha512-bY6fj56OUQ0hU1KjFNDQuJFezqKdrAyFdIevADiqrWHwSlbmBNMHp5ak2f40Pm8JTFyM2mqxkG6ngkHO11f/lg==",
+          "dev": true
+        },
+        "ansi-styles": {
+          "version": "4.3.0",
+          "resolved": "https://registry.npmjs.org/ansi-styles/-/ansi-styles-4.3.0.tgz",
+          "integrity": "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg==",
+          "dev": true,
+          "requires": {
+            "color-convert": "^2.0.1"
+          }
+        },
+        "chalk": {
+          "version": "3.0.0",
+          "resolved": "https://registry.npmjs.org/chalk/-/chalk-3.0.0.tgz",
+          "integrity": "sha512-4D3B6Wf41KOYRFdszmDqMCGq5VV/uMAB273JILmO+3jAlh8X4qDtdtgCR3fxtbLEMzSx22QdhnDcJvu2u1fVwg==",
+          "dev": true,
+          "requires": {
+            "ansi-styles": "^4.1.0",
+            "supports-color": "^7.1.0"
+          }
+        },
+        "color-convert": {
+          "version": "2.0.1",
+          "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-2.0.1.tgz",
+          "integrity": "sha512-RRECPsj7iu/xb5oKYcsFHSppFNnsj/52OVTRKb4zP5onXwVF3zVmmToNcOfGC+CRDpfK/U584fMg38ZHCaElKQ==",
+          "dev": true,
+          "requires": {
+            "color-name": "~1.1.4"
+          }
+        },
+        "color-name": {
+          "version": "1.1.4",
+          "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.4.tgz",
+          "integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==",
+          "dev": true
+        },
+        "has-flag": {
+          "version": "4.0.0",
+          "resolved": "https://registry.npmjs.org/has-flag/-/has-flag-4.0.0.tgz",
+          "integrity": "sha512-EykJT/Q1KjTWctppgIAgfSO0tKVuZUjhgMr17kqTumMl6Afv3EISleU7qZUzoXDFTAHTDC4NOoG/ZxU3EvlMPQ==",
+          "dev": true
+        },
+        "is-fullwidth-code-point": {
+          "version": "3.0.0",
+          "resolved": "https://registry.npmjs.org/is-fullwidth-code-point/-/is-fullwidth-code-point-3.0.0.tgz",
+          "integrity": "sha512-zymm5+u+sCsSWyD9qNaejV3DFvhCKclKdizYaJUuHA83RLjb7nSuGnddCHGv0hk+KY7BMAlsWeK4Ueg6EV6XQg==",
+          "dev": true
+        },
+        "string-width": {
+          "version": "4.2.2",
+          "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.2.tgz",
+          "integrity": "sha512-XBJbT3N4JhVumXE0eoLU9DCjcaF92KLNqTmFCnG1pf8duUxFGwtP6AD6nkjw9a3IdiRtL3E2w3JDiE/xi3vOeA==",
+          "dev": true,
+          "requires": {
+            "emoji-regex": "^8.0.0",
+            "is-fullwidth-code-point": "^3.0.0",
+            "strip-ansi": "^6.0.0"
+          }
+        },
+        "strip-ansi": {
+          "version": "6.0.0",
+          "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.0.tgz",
+          "integrity": "sha512-AuvKTrTfQNYNIctbR1K/YGTR1756GycPsg7b9bdV9Duqur4gv6aKqHXah67Z8ImS7WEz5QVcOtlfW2rZEugt6w==",
+          "dev": true,
+          "requires": {
+            "ansi-regex": "^5.0.0"
+          }
+        },
+        "supports-color": {
+          "version": "7.2.0",
+          "resolved": "https://registry.npmjs.org/supports-color/-/supports-color-7.2.0.tgz",
+          "integrity": "sha512-qpCAvRl9stuOHveKsn7HncJRvv501qIacKzQlO/+Lwxc9+0q2wLyv4Dfvt80/DPn2pqOBsJdDiogXGR9+OvwRw==",
+          "dev": true,
+          "requires": {
+            "has-flag": "^4.0.0"
+          }
+        }
+      }
+    },
     "brace-expansion": {
       "version": "1.1.11",
       "resolved": "https://registry.npmjs.org/brace-expansion/-/brace-expansion-1.1.11.tgz",
@@ -1652,6 +1815,38 @@
       "resolved": "https://registry.npmjs.org/bytes/-/bytes-3.1.0.tgz",
       "integrity": "sha512-zauLjrfCG+xvoyaqLoV8bLVXXNGC4JqlxFCutSDWA6fJrTo2ZuvLYTqZ7aHBLZSMOopbzwv8f+wZcVzfVTI2Dg=="
     },
+    "cacheable-request": {
+      "version": "6.1.0",
+      "resolved": "https://registry.npmjs.org/cacheable-request/-/cacheable-request-6.1.0.tgz",
+      "integrity": "sha512-Oj3cAGPCqOZX7Rz64Uny2GYAZNliQSqfbePrgAQ1wKAihYmCUnraBtJtKcGR4xz7wF+LoJC+ssFZvv5BgF9Igg==",
+      "dev": true,
+      "requires": {
+        "clone-response": "^1.0.2",
+        "get-stream": "^5.1.0",
+        "http-cache-semantics": "^4.0.0",
+        "keyv": "^3.0.0",
+        "lowercase-keys": "^2.0.0",
+        "normalize-url": "^4.1.0",
+        "responselike": "^1.0.2"
+      },
+      "dependencies": {
+        "get-stream": {
+          "version": "5.2.0",
+          "resolved": "https://registry.npmjs.org/get-stream/-/get-stream-5.2.0.tgz",
+          "integrity": "sha512-nBF+F1rAZVCu/p7rjzgA+Yb4lfYXrpl7a6VmJrU8wF9I1CKvP/QwPNZHnOlwbTkY6dvtFIzFMSyQXbLoTQPRpA==",
+          "dev": true,
+          "requires": {
+            "pump": "^3.0.0"
+          }
+        },
+        "lowercase-keys": {
+          "version": "2.0.0",
+          "resolved": "https://registry.npmjs.org/lowercase-keys/-/lowercase-keys-2.0.0.tgz",
+          "integrity": "sha512-tqNXrS78oMOE73NMxK4EMLQsQowWf8jKooH9g7xPavRT706R6bkQJ6DY2Te7QukaZsulxa30wQ7bk0pm4XiHmA==",
+          "dev": true
+        }
+      }
+    },
     "callsites": {
       "version": "3.1.0",
       "resolved": "https://registry.npmjs.org/callsites/-/callsites-3.1.0.tgz",
@@ -1760,6 +1955,18 @@
       "resolved": "https://registry.npmjs.org/chownr/-/chownr-1.1.1.tgz",
       "integrity": "sha1-VHJri4//TfBTxCGH6AH7RBLfFJQ="
     },
+    "ci-info": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/ci-info/-/ci-info-2.0.0.tgz",
+      "integrity": "sha512-5tK7EtrZ0N+OLFMthtqOj4fI2Jeb88C4CAZPu25LDVUgXJ0A3Js4PMGqrn0JU1W0Mh1/Z8wZzYPxqUrXeBboCQ==",
+      "dev": true
+    },
+    "cli-boxes": {
+      "version": "2.2.1",
+      "resolved": "https://registry.npmjs.org/cli-boxes/-/cli-boxes-2.2.1.tgz",
+      "integrity": "sha512-y4coMcylgSCdVinjiDBuR8PCC2bLjyGTwEmPb9NHR/QaNU6EUOXcTY/s6VjGMD6ENSEaeQYHCY0GNGS5jfMwPw==",
+      "dev": true
+    },
     "cli-cursor": {
       "version": "3.1.0",
       "resolved": "https://registry.npmjs.org/cli-cursor/-/cli-cursor-3.1.0.tgz",
@@ -1826,6 +2033,15 @@
         }
       }
     },
+    "clone-response": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/clone-response/-/clone-response-1.0.2.tgz",
+      "integrity": "sha1-0dyXOSAxTfZ/vrlCI7TuNQI56Ws=",
+      "dev": true,
+      "requires": {
+        "mimic-response": "^1.0.0"
+      }
+    },
     "cls-bluebird": {
       "version": "2.1.0",
       "resolved": "https://registry.npmjs.org/cls-bluebird/-/cls-bluebird-2.1.0.tgz",
@@ -1931,6 +2147,20 @@
         }
       }
     },
+    "configstore": {
+      "version": "5.0.1",
+      "resolved": "https://registry.npmjs.org/configstore/-/configstore-5.0.1.tgz",
+      "integrity": "sha512-aMKprgk5YhBNyH25hj8wGt2+D52Sw1DRRIzqBwLp2Ya9mFmY8KPvvtvmna8SxVR9JMZ4kzMD68N22vlaRpkeFA==",
+      "dev": true,
+      "requires": {
+        "dot-prop": "^5.2.0",
+        "graceful-fs": "^4.1.2",
+        "make-dir": "^3.0.0",
+        "unique-string": "^2.0.0",
+        "write-file-atomic": "^3.0.0",
+        "xdg-basedir": "^4.0.0"
+      }
+    },
     "console-control-strings": {
       "version": "1.1.0",
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@@ -2014,6 +2244,12 @@
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+    "write-file-atomic": {
+      "version": "3.0.3",
+      "resolved": "https://registry.npmjs.org/write-file-atomic/-/write-file-atomic-3.0.3.tgz",
+      "integrity": "sha512-AvHcyZ5JnSfq3ioSyjrBkH9yW4m7Ayk8/9My/DD9onKeu/94fwrMocemO2QAJFAlnnDN+ZDS+ZjAR5ua1/PV/Q==",
+      "dev": true,
+      "requires": {
+        "imurmurhash": "^0.1.4",
+        "is-typedarray": "^1.0.0",
+        "signal-exit": "^3.0.2",
+        "typedarray-to-buffer": "^3.1.5"
+      }
+    },
+    "xdg-basedir": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/xdg-basedir/-/xdg-basedir-4.0.0.tgz",
+      "integrity": "sha512-PSNhEJDejZYV7h50BohL09Er9VaIefr2LMAf3OEmpCkjOi34eYyQYAXUTjEQtZJTKcF0E2UKTh+osDLsgNim9Q==",
+      "dev": true
+    },
     "xregexp": {
       "version": "4.3.0",
       "resolved": "https://registry.npmjs.org/xregexp/-/xregexp-4.3.0.tgz",
@@ -7491,6 +8282,17 @@
           "dev": true,
           "requires": {
             "p-limit": "^2.0.0"
+          },
+          "dependencies": {
+            "p-limit": {
+              "version": "2.3.0",
+              "resolved": "https://registry.npmjs.org/p-limit/-/p-limit-2.3.0.tgz",
+              "integrity": "sha512-//88mFWSJx8lxCzwdAABTJL2MyWB12+eIY7MDL2SqLmAkeKU9qxRvWuSyTjm3FUmpBEMuFfckAIqEaVGUDxb6w==",
+              "dev": true,
+              "requires": {
+                "p-try": "^2.0.0"
+              }
+            }
           }
         },
         "string-width": {
diff --git a/services/clsi/package.json b/services/clsi/package.json
index 3afa29c459..dac3ba9dbb 100644
--- a/services/clsi/package.json
+++ b/services/clsi/package.json
@@ -31,6 +31,7 @@
     "lodash": "^4.17.20",
     "logger-sharelatex": "^2.2.0",
     "mysql": "^2.18.1",
+    "p-limit": "^3.1.0",
     "request": "^2.88.2",
     "sequelize": "^5.21.5",
     "settings-sharelatex": "^1.1.0",
@@ -58,6 +59,7 @@
     "eslint-plugin-react": "^7.19.0",
     "eslint-plugin-standard": "^4.0.1",
     "mocha": "^7.1.0",
+    "nodemon": "^2.0.7",
     "prettier": "^2.0.0",
     "prettier-eslint-cli": "^5.0.0",
     "sandboxed-module": "^2.0.3",
diff --git a/services/clsi/test/unit/js/ContentCacheManagerTests.js b/services/clsi/test/unit/js/ContentCacheManagerTests.js
index a7b25eacbc..35f22fffae 100644
--- a/services/clsi/test/unit/js/ContentCacheManagerTests.js
+++ b/services/clsi/test/unit/js/ContentCacheManagerTests.js
@@ -48,16 +48,19 @@ describe('ContentCacheManager', function () {
       }
     })
   }
-  let contentRanges, newContentRanges
+  let contentRanges, newContentRanges, reclaimed
   function run(filePath, done) {
     ContentCacheManager.update(contentDir, filePath, (err, ranges) => {
       if (err) return done(err)
-      ;[contentRanges, newContentRanges] = ranges
+      let newlyReclaimed
+      ;[contentRanges, newContentRanges, newlyReclaimed] = ranges
+      reclaimed += newlyReclaimed
       done()
     })
   }
 
   beforeEach(function () {
+    reclaimed = 0
     contentDir =
       '/app/output/602cee6f6460fca0ba7921e6/content/1797a7f48f9-5abc1998509dea1f'
     pdfPath =
@@ -70,6 +73,18 @@ describe('ContentCacheManager', function () {
     fs = {
       createReadStream: sinon.stub().returns(Readable.from([])),
       promises: {
+        async writeFile(name, blob) {
+          const file = new FakeFile()
+          await file.write(Buffer.from(blob))
+          await file.close()
+          files[name] = file
+        },
+        async readFile(name) {
+          if (!files[name]) {
+            throw new Error()
+          }
+          return files[name].toJSON().contents
+        },
         async open(name) {
           files[name] = new FakeFile()
           return files[name]
@@ -86,7 +101,12 @@ describe('ContentCacheManager', function () {
           files[newName] = files[oldName]
           delete files[oldName]
         },
-        unlink: sinon.stub().resolves()
+        async unlink(name) {
+          if (!files[name]) {
+            throw new Error()
+          }
+          delete files[name]
+        }
       }
     }
   })
@@ -99,9 +119,12 @@ describe('ContentCacheManager', function () {
 
     describe('when the ranges are split across chunks', function () {
       const RANGE_1 = 'stream123endstream'
-      const RANGE_2 = 'stream(|)endstream'
-      const RANGE_3 = 'stream!$%endstream'
-      beforeEach(function (done) {
+      const RANGE_2 = 'stream(||)endstream'
+      const RANGE_3 = 'stream!$%/=endstream'
+      const h1 = hash(RANGE_1)
+      const h2 = hash(RANGE_2)
+      const h3 = hash(RANGE_3)
+      function runWithSplitStream(done) {
         fs.createReadStream
           .withArgs(pdfPath)
           .returns(
@@ -109,12 +132,15 @@ describe('ContentCacheManager', function () {
               Buffer.from('abcstr'),
               Buffer.from('eam123endstreamABC'),
               Buffer.from('str'),
-              Buffer.from('eam(|'),
+              Buffer.from('eam(||'),
               Buffer.from(')end'),
-              Buffer.from('stream-_~stream!$%endstream')
+              Buffer.from('stream-_~stream!$%/=endstream')
             ])
           )
         run(pdfPath, done)
+      }
+      beforeEach(function (done) {
+        runWithSplitStream(done)
       })
 
       it('should produce three ranges', function () {
@@ -130,12 +156,12 @@ describe('ContentCacheManager', function () {
           },
           {
             start: 24,
-            end: 42,
+            end: 43,
             hash: hash(RANGE_2)
           },
           {
-            start: 45,
-            end: 63,
+            start: 46,
+            end: 66,
             hash: hash(RANGE_3)
           }
         ])
@@ -143,17 +169,32 @@ describe('ContentCacheManager', function () {
 
       it('should store the contents', function () {
         expect(JSON.parse(JSON.stringify(files))).to.deep.equal({
-          [Path.join(contentDir, hash(RANGE_1))]: {
+          [Path.join(contentDir, h1)]: {
             contents: RANGE_1,
             closed: true
           },
-          [Path.join(contentDir, hash(RANGE_2))]: {
+          [Path.join(contentDir, h2)]: {
             contents: RANGE_2,
             closed: true
           },
-          [Path.join(contentDir, hash(RANGE_3))]: {
+          [Path.join(contentDir, h3)]: {
             contents: RANGE_3,
             closed: true
+          },
+          [Path.join(contentDir, '.state.v0.json')]: {
+            contents: JSON.stringify({
+              hashAge: [
+                [h1, 0],
+                [h2, 0],
+                [h3, 0]
+              ],
+              hashSize: [
+                [h1, 18],
+                [h2, 19],
+                [h3, 20]
+              ]
+            }),
+            closed: true
           }
         })
       })
@@ -161,6 +202,140 @@ describe('ContentCacheManager', function () {
       it('should mark all ranges as new', function () {
         expect(contentRanges).to.deep.equal(newContentRanges)
       })
+
+      describe('when re-running with one stream removed', function () {
+        function runWithOneSplitStreamRemoved(done) {
+          fs.createReadStream
+            .withArgs(pdfPath)
+            .returns(
+              Readable.from([
+                Buffer.from('abcstr'),
+                Buffer.from('eam123endstreamABC'),
+                Buffer.from('stream!$%/=endstream')
+              ])
+            )
+          run(pdfPath, done)
+        }
+        beforeEach(function (done) {
+          runWithOneSplitStreamRemoved(done)
+        })
+
+        it('should produce two ranges', function () {
+          expect(contentRanges).to.have.length(2)
+        })
+
+        it('should find the correct offsets', function () {
+          expect(contentRanges).to.deep.equal([
+            {
+              start: 3,
+              end: 21,
+              hash: hash(RANGE_1)
+            },
+            {
+              start: 24,
+              end: 44,
+              hash: hash(RANGE_3)
+            }
+          ])
+        })
+
+        it('should update the age of the 2nd range', function () {
+          expect(JSON.parse(JSON.stringify(files))).to.deep.equal({
+            [Path.join(contentDir, h1)]: {
+              contents: RANGE_1,
+              closed: true
+            },
+            [Path.join(contentDir, h2)]: {
+              contents: RANGE_2,
+              closed: true
+            },
+            [Path.join(contentDir, h3)]: {
+              contents: RANGE_3,
+              closed: true
+            },
+            [Path.join(contentDir, '.state.v0.json')]: {
+              contents: JSON.stringify({
+                hashAge: [
+                  [h1, 0],
+                  [h2, 1],
+                  [h3, 0]
+                ],
+                hashSize: [
+                  [h1, 18],
+                  [h2, 19],
+                  [h3, 20]
+                ]
+              }),
+              closed: true
+            }
+          })
+        })
+
+        it('should find no new ranges', function () {
+          expect(newContentRanges).to.deep.equal([])
+        })
+
+        describe('when re-running 5 more times', function () {
+          for (let i = 0; i < 5; i++) {
+            beforeEach(function (done) {
+              runWithOneSplitStreamRemoved(done)
+            })
+          }
+
+          it('should still produce two ranges', function () {
+            expect(contentRanges).to.have.length(2)
+          })
+
+          it('should still find the correct offsets', function () {
+            expect(contentRanges).to.deep.equal([
+              {
+                start: 3,
+                end: 21,
+                hash: hash(RANGE_1)
+              },
+              {
+                start: 24,
+                end: 44,
+                hash: hash(RANGE_3)
+              }
+            ])
+          })
+
+          it('should delete the 2nd range', function () {
+            expect(JSON.parse(JSON.stringify(files))).to.deep.equal({
+              [Path.join(contentDir, h1)]: {
+                contents: RANGE_1,
+                closed: true
+              },
+              [Path.join(contentDir, h3)]: {
+                contents: RANGE_3,
+                closed: true
+              },
+              [Path.join(contentDir, '.state.v0.json')]: {
+                contents: JSON.stringify({
+                  hashAge: [
+                    [h1, 0],
+                    [h3, 0]
+                  ],
+                  hashSize: [
+                    [h1, 18],
+                    [h3, 20]
+                  ]
+                }),
+                closed: true
+              }
+            })
+          })
+
+          it('should find no new ranges', function () {
+            expect(newContentRanges).to.deep.equal([])
+          })
+
+          it('should yield the reclaimed space', function () {
+            expect(reclaimed).to.equal(RANGE_2.length)
+          })
+        })
+      })
     })
   })
 })