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Degraded Performance

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Maintenance

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Partial out­age

No down­time recorded on this day.

No data ex­ists for this day.

had a ma­jor out­age.

had a par­tial out­age.

Past Incidents

May 27, 2026

No in­ci­dents re­ported to­day.

May 26, 2026

Resolved - This in­ci­dent has been re­solved. Thank you for your pa­tience and un­der­stand­ing as we ad­dressed this is­sue. A de­tailed root cause analy­sis will be shared as soon as it is avail­able.

May 26, 16:35 UTC

Monitoring - The degra­da­tion af­fect­ing Copilot has been mit­i­gated. We are mon­i­tor­ing to en­sure sta­bil­ity.

May 26, 16:24 UTC

Update - Copilot is ex­pe­ri­enc­ing de­graded per­for­mance. We are con­tin­u­ing to in­ves­ti­gate.

May 26, 15:48 UTC

Investigating - We are in­ves­ti­gat­ing re­ports of im­pacted per­for­mance for some GitHub ser­vices.

May 26, 15:44 UTC

Resolved - This in­ci­dent has been re­solved. Thank you for your pa­tience and un­der­stand­ing as we ad­dressed this is­sue. During this in­ci­dent, a small num­ber of Issues, PRs, Comments, and Discussions were marked as hid­den. We are work­ing on cor­rect­ing the un­der­ly­ing records. No data has been lost as part of this in­ci­dent. A de­tailed root cause analy­sis will be shared as soon as it is avail­able.

May 26, 13:18 UTC

Update - The degra­da­tion has been mit­i­gated. We are mon­i­tor­ing to en­sure sta­bil­ity.

May 26, 13:01 UTC

Monitoring - The degra­da­tion af­fect­ing Actions and Pages has been mit­i­gated. We are mon­i­tor­ing to en­sure sta­bil­ity.

May 26, 13:00 UTC

Update - We have iden­ti­fied the cause of the au­then­ti­ca­tion is­sues af­fect­ing GitHub Actions and are ac­tively work­ing on mit­i­ga­tion

May 26, 12:37 UTC

Update - Actions is ex­pe­ri­enc­ing de­graded per­for­mance. We are con­tin­u­ing to in­ves­ti­gate.

May 26, 12:17 UTC

Update - We are in­ves­ti­gat­ing au­then­ti­ca­tion is­sues lead­ing to fail­ure in start­ing Actions runs and down­load­ing ac­tions. At this time the ma­jor­ity of Actions runs is im­pacted.

May 26, 11:53 UTC

Update - Actions is ex­pe­ri­enc­ing de­graded avail­abil­ity. We are con­tin­u­ing to in­ves­ti­gate.

May 26, 11:19 UTC

Investigating - We are in­ves­ti­gat­ing re­ports of de­graded per­for­mance for Actions and Pages

May 26, 10:57 UTC

May 25, 2026

No in­ci­dents re­ported.

May 24, 2026

No in­ci­dents re­ported.

May 23, 2026

Resolved - This in­ci­dent has been re­solved. Thank you for your pa­tience and un­der­stand­ing as we ad­dressed this is­sue. A de­tailed root cause analy­sis will be shared as soon as it is avail­able.

May 23, 19:32 UTC

Update - This is fully mit­i­gated, we will con­tinue to mon­i­tor to en­sure it does not re­oc­cur.

May 23, 19:32 UTC

Update - We have iden­ti­fied and are ap­ply­ing ad­di­tional mit­i­ga­tion and will con­tinue to mon­i­tor for com­plete mit­i­ga­tion.

May 23, 19:06 UTC

Update - We see sig­nif­i­cant signs of mit­i­ga­tion and are mon­i­tor­ing for full mit­i­ga­tion.

May 23, 18:42 UTC

Update - We are see­ing signs of mit­i­ga­tion and are con­tin­u­ing to mon­i­tor for com­plete mit­i­ga­tion.

Next up­date in one hour.

Update - We are con­tin­u­ing to in­ves­ti­gate an el­e­vated er­ror rate of au­then­ti­ca­tion fail­ures for app in­stal­la­tion to­kens.  Next up­date in one hour.

May 23, 16:35 UTC

Update - We are see­ing an in­creased rate of au­then­ti­ca­tion fail­ures for app in­stal­la­tion to­kens, af­fect­ing ap­prox­i­mately 1% of to­kens.  We are con­tin­u­ing to in­ves­ti­gate.

May 23, 16:01 UTC

Investigating - We are in­ves­ti­gat­ing re­ports of im­pacted per­for­mance for some GitHub ser­vices.

May 23, 16:00 UTC

May 22, 2026

No in­ci­dents re­ported.

May 21, 2026

No in­ci­dents re­ported.

May 20, 2026

Resolved - On May 20, 2026, be­tween 16:00 UTC and 17:45 UTC, GitHub Actions cus­tomers ex­pe­ri­enced run start de­lays ex­ceed­ing 5 min­utes. Approximately 4.5% of all runs were de­layed dur­ing the im­pact win­dow, with scale set jobs dis­pro­por­tion­ately af­fected. 30% of scale set jobs were de­layed and 4% failed to start en­tirely.

The in­ci­dent was caused by a mis­con­fig­ured health check on an in­ter­nal ser­vice that as­signs jobs to run­ners. A brief la­tency spike in an up­stream de­pen­dency trig­gered health check fail­ures across sev­eral pods, re­mov­ing them from ser­vice and con­cen­trat­ing load on the re­main­ing ca­pac­ity. The added load drove mem­ory pres­sure that es­ca­lated into a cas­cad­ing fail­ure in one re­gional clus­ter, leav­ing it un­able to self-re­cover.

Responders mit­i­gated the in­ci­dent by scal­ing ca­pac­ity in the healthy re­gional clus­ters and drain­ing traf­fic away from the im­paired one, af­ter which run start la­tency re­cov­ered. To pre­vent re­cur­rence, we are strength­en­ing our health check con­fig­u­ra­tion to avoid cas­cad­ing fail­ure sce­nar­ios and eval­u­at­ing au­to­mated mit­i­ga­tions to re­bal­ance traf­fic when a re­gion is de­graded.

Update - Customer im­pact has fully sub­sided. We are main­tain­ing yel­low sta­tus while we de­ploy a per­ma­nent fix to pre­vent re­cur­rence.

May 20, 19:41 UTC

Update - We’ve ap­plied a mit­i­ga­tion to fix the is­sues with queu­ing and run­ning Actions jobs. We are see­ing im­prove­ments in teleme­try and are mon­i­tor­ing for full re­cov­ery.

May 20, 18:17 UTC

Monitoring - The degra­da­tion af­fect­ing Actions has been mit­i­gated. We are mon­i­tor­ing to en­sure sta­bil­ity.

May 20, 17:52 UTC

Tony Blair’s con­sul­tancy dou­bles down on AI and re­struc­tures in Europe

The move will af­fect its re­cently opened Brussels of­fice.

May 22

1 min read

EU so­cial me­dia ban could come this sum­mer, von der Leyen says

Commission chief says EU can learn from “pioneer” Australia in im­pos­ing min­i­mum age for so­cial me­dia.

May 12

2 mins read

OpenAI of­fers EU ac­cess to new AI hack­ing model

European cy­ber and AI au­thor­i­ties in past weeks failed to gain ac­cess to su­per­hack­ing AI, caus­ing anx­i­ety among of­fi­cials.

May 11

3 mins read

You’ve prob­a­bly heard some­one say some­thing to the ef­fect of “renting is just throw­ing your money away”. Don’t be­lieve it. It’s a glib state­ment that sim­ply is­n’t true. There are so many hid­den costs to home own­er­ship that most peo­ple who have never owned a home don’t know about. If you want to make an in­formed de­ci­sion about whether to buy a home or keep rent­ing, then you need to un­der­stand these costs. I’ll break them down for you in this post, show­ing my ac­tual costs.

Expenses

Mortgage Loan Fees

Getting a loan is not cheap. When I bought my home, the to­tal set­tle­ment costs were about 3% of the value of the home. Here is the break­down of my loan costs when I bought my house. Keep in mind this was way back in early 2011, so cur­rent costs are un­doubt­edly higher:

That’s $12,777.92 to get the loan.

Mortgage Payment

When you get a loan to buy a house, you pay for two main things each month: prin­ci­pal and in­ter­est. The prin­ci­pal re­duces how much you owe, and the in­ter­est is what the bank earns for lend­ing you the money. I don’t con­sider prin­ci­pal an ex­pense, since pay­ing it does­n’t change your net worth. Sure, your check­ing ac­count has less money in it, but you also have less debt.

Interest, on the other hand, is an ex­pense. It low­ers your net worth. About 80% of your first mort­gage pay­ment is in­ter­est. Not much dif­fer­ent than rent­ing at first. Over time, you’ll pay less in­ter­est and more prin­ci­pal, but for the first few years you’ll be sur­prised how lit­tle you ac­tu­ally re­duce the amount you owe.

You may also have to pay Private Mortgage Insurance (PMI) if you don’t have a large enough down pay­ment. When I bought my house, you needed to put down 20% of the home price to avoid pay­ing PMI.

Usually your other ex­penses such as taxes and in­sur­ance are in­cluded in your monthly pay­ment, and paid into es­crow each month. Insurance and taxes are au­to­mat­i­cally paid out of es­crow for you once or twice a year.

My first mort­gage pay­ment in January 2011 was:

That’s $2,329.92 per month.

Less than 21% of my monthly pay­ment was go­ing to­ward pay­ing off the loan! $1,847.28 of that was pure ex­pense; a re­duc­tion of my net worth. At the time I bought my house, I was pay­ing about the same amount for a very nice one-bed­room apart­ment in down­town Baltimore with a view of the down­town sky­line, the base­ball sta­dium, and the har­bor. It makes that rent-vs-buy de­ci­sion a lot less clear-cut.

I no longer pay PMI. You can re­quest that they re­move it when you think your eq­uity in the home is 20% or more, or they will even­tu­ally re­move it. The bank may charge you to have your house as­sessed.

I pay $113.05 less per month with­out PMI, but tax and in­sur­ance al­ways goes up. I cur­rently pay $515.50 per month for tax, $111.17 per month for in­sur­ance, and $31.36 per month of es­crow short­age (your es­crow amount to pay taxes and in­sur­ance is es­ti­mated each year, and if they don’t es­ti­mate cor­rectly then they add an over­age/​short­age charge each month to cor­rect it).

My cur­rent to­tal mort­gage pay­ment is $2,440.48.

Insurance

Insurance is re­quired by the lender, but even if your house is paid off you should have in­sur­ance. The cost of in­sur­ance in­creases every year.

You may at some point be re­quired to make im­prove­ments (e.g. re­place your roof) to keep your in­sur­ance.

I cur­rently pay $111.17 per month for home­own­er’s in­sur­ance.

Taxes

If you’re buy­ing a house that was just built, be aware that the past prop­erty taxes on record won’t re­flect how much you will ac­tu­ally pay for taxes. Your prop­erty value will be re­assessed, and the new as­sessed value (which taxes are based on) will in­clude the new struc­ture.

Taxes go up every year too. Try to find out if there’s a pro­gram to cap prop­erty as­sess­ment in­creases and/​or tax rate in­creases. In my area it’s called the Homestead Tax Credit.

I cur­rently pay $515.50 per month for prop­erty taxes.

Maintenance & Repairs

General wis­dom is to plan to save at least 1% of the value of your home each year to cover cur­rent and fu­ture main­te­nance and re­pairs. Older homes may have de­ferred main­te­nance or re­pairs that needs to be ad­dressed, or have more undis­cov­ered or up­com­ing main­te­nance or re­pairs to ex­pect. In that case you should plan to save at a higher rate.

My 1983 home had been used as a rental for years, so much of the main­te­nance had been ne­glected. Here are some ex­am­ples of the main­te­nance and re­pairs I’ve had done on my house:

Replaced leak­ing sky­lights: $6,566

New roof: $9,390

New win­dows: $10,530

New sid­ing: $21,046

Cut down trees that were too close to the house: $2,800

Replaced poly­buty­lene wa­ter pipes: $5,050

New gut­ters: $2,714

Replaced drain pump in the dish­washer: $95

Replaced leak­ing faucet: $185

Replaced fail­ing HVAC con­trol board: $65

Yard main­te­nance (e.g. mulch, weed con­trol, mow­ing, etc): prob­a­bly around $500/year

Fixed handrail for the ex­te­rior base­ment stair­well: $85

You can save a lot of money in main­te­nance and re­pairs by do­ing your own work when­ever pos­si­ble. I re­placed the drain pump in my dish­washer, re­placed a leak­ing kitchen faucet, re­placed the con­trol board on my HVAC sys­tem, do all my own yard work, etc.

Improvements

You may want to put up a fence, a gar­den shed, pave a gravel dri­ve­way, re­model a kitchen or bath­room, etc. These im­prove­ments are in ad­di­tion to the main­te­nance and re­pairs. If you’re the type of per­son who wants their fur­nish­ings, decor, ap­pli­ances, etc to be styl­ish, ex­pect to pay for im­prove­ments fairly of­ten. Here are some of the im­prove­ments I’ve done on my house:

Painted rooms

Replaced base­board mould­ings

Remodeled the guest bath­room

Installed new ceil­ing fan in the liv­ing room

New cur­tains and blinds

Extended kitchen cab­i­nets

Raised kitchen cup­boards

Installed more light­ing in the kitchen

Reworked laun­dry plumb­ing

Installed a util­ity sink in the laun­dry room

Installed cup­boards in the laun­dry room

Installed a new sink in the kitchen

New gran­ite coun­ters in the kitchen

Built a new deck

Built a new front step

Installed sky­light shades

Various yard im­prove­ments (e.g. new plants)

Doing the work your­self can save you a lot of money here too. For ex­am­ple, I built the deck on my house for about $15k, which was roughly 1/2 the cost of the av­er­age es­ti­mates I re­ceived to have it built for me.

Higher Utility Costs

Houses are al­most al­ways larger than apart­ments, and re­quire more en­ergy to heat/​cool. Expect to pay more sim­ply be­cause of that. I sus­pect heat­ing and cool­ing ac­count for about half of my elec­tric­ity use.

Rates keep in­creas­ing too. This af­fects home own­ers and renters, but it hits harder when you’re heat­ing or cool­ing a larger house. The old­est bill I could find was from January 2024. Back then I was pay­ing about 17.3¢ per kWh, in­clud­ing all the fees and taxes. On my last bill for May 2026, I paid 24.7¢ per kWh. In only two years, my elec­tric­ity rates have gone up 42% 😲. I only ex­pect this to get worse, since the rates here are (partly) de­ter­mined by an auc­tion process that is af­fected by the de­mand for new data cen­ters to sup­port the cur­rent AI ex­plo­sion.

Selling

Most peo­ple don’t keep their home for­ever. When you move, ex­pect to pay up­wards of 10% of the value of the home just to sell it!

I sold my home in Auburn, WA back in 2007, right as the hous­ing cri­sis was ramp­ing up. I was lucky to find a buyer will­ing to pay a rea­son­able price for my house. I bought this house new, and did­n’t live there very long, so it did­n’t need any prepa­ra­tion to be ready for the mar­ket. Here are some costs I paid to sell my house:

That’s $26,038.17 in costs to sell my home, not in­clud­ing the costs for mov­ing (e.g. stor­age, ship­ping, etc).

Legal

If you have any con­flict with neigh­bors (e.g. prop­erty bound­ary, trees, etc), you may need to hire an at­tor­ney, sur­vey­ors, etc.

Appreciation

We hope that value of our homes in­creases over time. Home val­ues have risen an av­er­age of 3.8% per year since 1991. That’s not a guar­an­tee, and it de­pends on tim­ing when you buy and sell, where the home is, and more.

I bought my home in Auburn, WA for $321k, and sold it a few years later for $333k. After all the costs to buy and sell it, I prob­a­bly lost more money on it than I would have spent rent­ing an apart­ment.

I bought my cur­rent home in 2011 for $420k, and the Zillow cur­rently es­ti­mates its value at $757k. I’ve put a lot of money into it catch­ing up on main­te­nance, re­pairs, and im­prove­ments, but the ap­pre­ci­a­tion will def­i­nitely ex­ceed what­ever I’ve put into it when I de­cide to sell it.

You should plan to live in your home long enough for the in­crease in value to ex­ceed the ex­penses.

Should You Buy a Home?

If you buy a de­cent house in a de­cent area, and plan to live there for quite a while, then buy­ing a home could make sense.

Aside from the fi­nan­cial pros and cons, you have to con­sider the qual­ity of life. More space and a qui­eter en­vi­ron­ment are two very big ad­van­tages of own­ing a home in the right lo­ca­tion.

Andrew Gleeson de­signed Analog Mono, “fixing the crimes of VCR OSD Mono.” There used to be this clas­sic pixel font that you’d see every­where in the 1990s on hi-fi equip­ment: VCRs, TVs, cam­corders, etc. One of its chal­lenges was a low base­line which re­sulted in all the let­ters with de­scen­ders pulled up, for ex­am­ple:

Analog Mono fixes that prob­lem:

Elsewhere, Kumiko Yoshida made Coral Pixels (also on Google Fonts), a color font that comes with the 1990s and 2000s col­or­ful fring­ing baked in. The fring­ing was once an ar­ti­fact of sub­pixel ren­der­ing, but now it is meant to evoke nos­tal­gia or just as an in­ter­est­ing vi­sual el­e­ment in and of it­self. (Perhaps ad­ja­cent to chro­matic aber­ra­tion?)

Lastly, here’s Two Slice by Joseph Fatula — a font that’s only 2 pix­els tall, “and some­what read­able.”

Of course, these are all vec­tor fonts — e.g. ready to be in­stalled on a mod­ern op­er­at­ing sys­tem — pre­tend­ing to be pixel fonts. That’s maybe a sep­a­rate post al­to­gether, but it leads us to the last font, Geist Pixel from Vercel:

The copy in­tro­duc­ing the font is a lit­tle pre­ten­tious/​​spicy, but it touches upon some­thing im­por­tant:

Geist Pixel is­n’t a nov­elty font. It’s a sys­tem ex­ten­sion. [… It] was de­signed with real us­age in mind, not as a vi­sual gim­mick, but as a func­tional tool within a broader ty­po­graphic sys­tem. […] This mat­ters be­cause pixel fonts of­ten break in pro­duc­tion. They don’t scale prop­erly across view­ports, their met­rics con­flict with ex­ist­ing ty­pog­ra­phy, or they’re purely dec­o­ra­tive. Geist Pixel was built to solve these prob­lems, main­tain­ing the vi­sual tex­ture teams want while pre­serv­ing the ty­po­graphic rigor prod­ucts re­quire.

Geist Pixel is­n’t a nov­elty font. It’s a sys­tem ex­ten­sion. [… It] was de­signed with real us­age in mind, not as a vi­sual gim­mick, but as a func­tional tool within a broader ty­po­graphic sys­tem. […] This mat­ters be­cause pixel fonts of­ten break in pro­duc­tion. They don’t scale prop­erly across view­ports, their met­rics con­flict with ex­ist­ing ty­pog­ra­phy, or they’re purely dec­o­ra­tive. Geist Pixel was built to solve these prob­lems, main­tain­ing the vi­sual tex­ture teams want while pre­serv­ing the ty­po­graphic rigor prod­ucts re­quire.

There are def­i­nitely fonts whose Achilles’ heel is not the let­ter­forms, but the in­vis­i­ble hard work put into every­thing that sur­rounds them: the kern­ing, the meta­data, the ex­tra glyphs, the ver­ti­cal met­rics. It seems that the team be­ing Geist Pixel is proud of es­pe­cially that last part.

Dropbox Co-CEOs Ashraf Alkarmi and Drew Houston. Houston will even­tu­ally step down and as­sume the role of ex­ec­u­tive chair­man at the com­pany he helmed for 19 years.

Courtesy: Dropbox

Drew Houston founded Dropbox nearly two decades ago at age 24, even­tu­ally be­com­ing a house­hold name in Silicon Valley and the first tech en­tre­pre­neur to take a com­pany from the Y Combinator in­cu­ba­tor pro­gram all the way to the pub­lic mar­ket.

Now, at 43, Houston is ready to do some­thing else. He’s in­form­ing staffers on Tuesday that he’ll be tran­si­tion­ing into an ex­ec­u­tive chair­man role af­ter an ini­tial pe­riod shar­ing the co-CEO ti­tle with Ashraf Alkarmi, who is be­ing pro­moted from prod­uct chief. Alkarmi will even­tu­ally take over the top job on his own.

By al­most any mea­sure, Houston has had a great run at Dropbox, help­ing pi­o­neer the cloud stor­age mar­ket, com­pet­ing head-to-head with Google and Apple and build­ing a net worth of more than $2 bil­lion, thanks to sub­stan­tial own­er­ship in his com­pany. But in the land of out­sized ex­pec­ta­tions, Houston has over­seen a com­pany that peaked too soon and never be­came a gen­er­a­tion-defin­ing brand.

Dropbox’s cur­rent mar­ket cap of just over $6 bil­lion is down by half from the high price on its first day of trad­ing in 2018, and is be­low the $10 bil­lion val­u­a­tion it was as­cribed by pri­vate mar­ket in­vestors in 2014. Meanwhile, Airbnb, an­other early break­out hit from Y Combinator, has a mar­ket cap of close to $80 bil­lion, and CEO Brian Chesky is cred­ited with up­end­ing the hos­pi­tal­ity in­dus­try.

Houston, who cre­ated Dropbox due to a “personal frus­tra­tion” with con­stantly los­ing USB sticks when he was in col­lege at the Massachusetts Institute of Technology, brushed off the Airbnb com­par­i­son.

“I think my 18-year-old self would be high-fiv­ing me,” Houston told CNBC in an ex­clu­sive in­ter­view, not­ing that Dropbox is “something that a per­cent­age of the planet still uses.”

In its lat­est quar­terly earn­ings re­port, Dropbox said it has more than 18 mil­lion pay­ing users, and the ser­vice re­mains pop­u­lar with me­dia pro­fes­sion­als, graphic de­sign­ers, ar­chi­tects, and oth­ers who share files and pho­tos as part of their daily work.

Dropbox CEO Drew Houston Dropbox and co-founder Arash Ferdowsi (together at cen­ter) cel­e­brate the launch of Dropbox’s ini­tial pub­lic of­fer­ing as they ring the open­ing bell at Nasdaq MarketSite, March 23, 2018 in New York City.

Drew Angerer | Getty Images News | Getty Images

Dropbox topped $1 bil­lion in an­nual rev­enue in 2017 and sur­passed $2 bil­lion four years later. But rev­enue is roughly flat over the past two years and de­clined slightly in 2025.

The com­pa­ny’s per­pet­ual chal­lenge has been to dis­tin­guish it­self from the swarm of com­pe­ti­tion, which in­cludes Apple and Google as well as Amazon and Microsoft. Then there’s long­time ri­val Box, which is still run by founder Aaron Levie and faces sim­i­lar ob­sta­cles. Box is val­ued at just over $3.5 bil­lion.

The lat­est hur­dle for Dropbox, and the whole cat­e­gory of sub­scrip­tion soft­ware, is ar­ti­fi­cial in­tel­li­gence, which has swept across the tech in­dus­try over the past three-plus years. The soft­ware space has been ham­mered due to con­cerns that foun­da­tion mod­els from OpenAI and Anthropic will en­able sim­pler tools that dis­place ex­ist­ing prod­ucts.

Dropbox shares have held up bet­ter than many in the en­ter­prise space. The stock is down less than 5% in the past year, while com­pa­nies like Monday.com, HubSpot and Asana have lost more than 60% of their value.

“Whenever there’s a new tech­nol­ogy, peo­ple ex­trap­o­late very quickly,” Houston said. They make as­sump­tions that may be “directionally cor­rect” but take years or even decades longer to play out than they pre­dict.

Regarding “this con­cept of SaaS Apocalypse or what­ever,” Houston said he’s “never met a Dropbox cus­tomer who’s like, ‘I’m just us­ing so much ChatGPT I’m go­ing to can­cel my Dropbox sub­scrip­tion.’”

‘Unanswerable ques­tion’

John Lovelock, an an­a­lyst at Gartner, sees par­al­lels be­tween the cur­rent AI era and the early days of cloud com­put­ing, when com­pa­nies like Salesforce bal­looned at the ex­pense of legacy ven­dors like Oracle and SAP. The tra­di­tional play­ers did­n’t col­lapse but saw growth slow as they tried to pivot to the cloud, de­spite busi­nesses spend­ing more on tech­nol­ogy.

The mar­ket is try­ing to pre­dict how things will play out with AI, Lovelock sug­gested.

“AI is go­ing to bring more value, there­fore there’s go­ing to be more money spent,” Lovelock said. “Where every­body seems to get very ex­cited is who’s go­ing to make that money and that, in some ways, is the unan­swer­able ques­tion right now.”

Analysts at Monness, Crespi, Hardt & Co. wrote in a re­port ear­lier this month af­ter earn­ings that Dropbox is “making progress,” high­light­ing its AI-powered Dash fea­ture that cus­tomers can use to more eas­ily search and in­ter­act with doc­u­ments and mes­sages across third-party apps. The an­a­lysts, who have the equiv­a­lent of a hold rat­ing on the stock, said the AI op­por­tu­nity and the com­pa­ny’s val­u­a­tion are two rea­sons that “value in­vestors may be drawn to Dropbox.”

Dash lets users quickly query and ma­nip­u­late con­tent that goes be­yond text and into video and au­dio.   Houston said ad­vance­ments in AI mod­els mean that “suddenly we can build the ver­sion of this that I would have loved to build 10 years ago.”

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Houston now plans on build­ing some­thing in AI, just not at Dropbox.

“I’m not go­ing to be rac­ing sail­boats,” said Houston, who’s also a board mem­ber at Meta, join­ing in 2020.

Houston said he wants to do some­thing en­tre­pre­neur­ial in AI be­cause “there’s never been a more ex­cit­ing pe­riod to be build­ing things.”

“It’s all cliche, right?” Houston said. “AI is re­shap­ing every as­pect of how we live, and I’m sure that I’ll have no short­age of ideas and stuff to work on.”

Along with Houston’s planned move, Dropbox said on Tuesday that Mike Torres is join­ing the com­pany from Google as chief prod­uct of­fi­cer in July. Torres is cur­rently vice pres­i­dent of prod­uct for Google’s Chrome.

As for when and why Houston made the de­ci­sion to leave, he said there was no spe­cific rea­son for the tim­ing.

“Part of me has al­ways thought, oh yeah, I’ll be the CEO of Dropbox un­til my last gasp of my ca­reer,” he said. “There’s never a per­fect time, there was no part of me where I was like, ‘oh, this date is the date where it’s go­ing to hap­pen.’”

Since Alkarmi joined Dropbox from Vimeo in late 2024, the com­pany has “become a lot more re­spon­sive to our cus­tomers and is tak­ing big­ger swings on in­no­va­tion,” Houston said.

“I trust the right leader,” he said. “The com­pa­ny’s in the right place.”

WATCH: Dropbox CEO Drew Houston on sub­scribers and AI-powered tools.

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May 26, 2026

The worst job in­ter­view I ever had was­n’t a knowl­edge melt­down, cod­ing as­sess­ment fail­ure, or a com­plete lan­guage mis­un­der­stand­ing with the in­ter­viewer (although I’ve had all of those, too). No, the worst job in­ter­view I had was some­thing I can only de­scribe as an un­so­licited psych eval­u­a­tion.

I’m an en­gi­neer, pri­mar­ily work­ing for small star­tups. At a less-than-10-per­son com­pany, es­pe­cially in the ear­li­est days, cul­tural fit is of sin­gu­lar im­por­tance. Even if you hire a cracked en­gi­neer, it’s prob­a­bly not gonna be a good ex­pe­ri­ence all-around if you can’t make a hu­man con­nec­tion. All this is to say - I get why you’d want to pri­or­i­tize this. But de­spite many quite nor­mal cul­ture fit in­ter­views, there’s one I still re­play in my con­fused head once in a while. And I think it’s worth shar­ing not be­cause I want to shame the com­pany or in­di­vid­u­als (I’ve left them anony­mous), but rather to sug­gest some re­con­sid­er­a­tion for founders and hir­ing man­agers in the same boat.

About 3 years ago, I re­sponded to a mes­sage look­ing for a found­ing en­gi­neer at a men­tal health startup (their no­ble cause was im­prov­ing ther­apy ac­cess for at-risk youth). The first in­ter­view was a quick con­ver­sa­tion with a founder and their head of en­gi­neer­ing — a fairly un­event­ful in­for­ma­tional in­ter­view (“this is why we’re great join us blah blah”). The fol­low-up with the head of en­gi­neer­ing was sched­uled shortly af­ter­wards.

The fol­low-up, they de­scribed over email, would be a bit non tra­di­tional - a ~90 minute cul­ture fit chat. Note there was no tech­ni­cal as­sess­ment yet. Expecting lit­tle, I joined the video call. It was ex­plained we’d just be get­ting to know each other based on some guid­ing ques­tions.

I fail to re­call the ex­act word­ing of the dis­cus­sion top­ics, but they were, in fact, non-tech­ni­cal — cov­er­ing such lovely top­ics as the hard­est day of my life, my biggest life chal­lenges, and other sim­i­lar “trauma-baiting” ques­tions.

Now, to be clear, I can un­der­stand why these dis­cus­sions might give deep in­sight into a can­di­date! It’s just that I think it’s frankly a lit­tle in­va­sive when you’re ba­si­cally meet­ing this per­son for the first time.

I’m a lit­tle ashamed re­mem­ber­ing my­self talk­ing about failed re­la­tion­ships, fam­ily strug­gles, and in­ter­per­sonal chal­lenges in pre­vi­ous work en­vi­ron­ments. This per­son gave the im­pres­sion that it was a safe space to share, di­vulging lit­tle of their own trauma.

By the end of the call I felt com­pletely emo­tion­ally drained - and i had­n’t even opened my ter­mi­nal! By the time I got the cur­sory one line “We won’t be mov­ing for­ward” email 24 hours later that emo­tional ex­haus­tion quickly turned into two new feel­ings: shame and anger.

I felt aw­ful that i had shared such deeply per­sonal things with the in­ter­viewer just to be cast off in a re­jec­tion email. I felt an­gry that I was re­jected. I felt em­bar­rass­ment that my soul was seem­ingly cracked open and judged “unworthy.” It was­n’t my skills they were re­ject­ing. It was… me.. I felt con­fused that a men­tal health startup had con­sciously de­cided to choose an in­ter­view so ca­pa­ble of mak­ing can­di­dates feel so vul­ner­a­ble.

I don’t think this per­son was try­ing to be cruel. Honestly, that al­most made it more con­fus­ing. The for­mat it­self cre­ated the prob­lem.

Culture fit is im­por­tant, make no mis­take. Make sure the peo­ple you hire are good peo­ple with strong morals. But con­sider eval­u­at­ing this in a way that does­n’t make can­di­dates feel like they need to share their deep­est ex­pe­ri­ences just to scrape and claw for em­ploy­ment.